diff --git a/.ci/scripts/calculate_jobs.py b/.ci/scripts/calculate_jobs.py
index 50e11e6504..661887e209 100755
--- a/.ci/scripts/calculate_jobs.py
+++ b/.ci/scripts/calculate_jobs.py
@@ -47,10 +47,9 @@ if not IS_PR:
             "database": "sqlite",
             "extras": "all",
         }
-        for version in ("3.9", "3.10", "3.11")
+        for version in ("3.9", "3.10", "3.11", "3.12.0-rc.1")
     )
 
-
 trial_postgres_tests = [
     {
         "python-version": "3.8",
diff --git a/.github/workflows/latest_deps.yml b/.github/workflows/latest_deps.yml
index ec6391cf8f..7b839f59c1 100644
--- a/.github/workflows/latest_deps.yml
+++ b/.github/workflows/latest_deps.yml
@@ -57,8 +57,8 @@ jobs:
       # `pip install matrix-synapse[all]` as closely as possible.
       - run: poetry update --no-dev
       - run: poetry run pip list > after.txt && (diff -u before.txt after.txt || true)
-      - name: Remove warn_unused_ignores from mypy config
-        run: sed '/warn_unused_ignores = True/d' -i mypy.ini
+      - name: Remove unhelpful options from mypy config
+        run: sed -e '/warn_unused_ignores = True/d' -e '/warn_redundant_casts = True/d' -i mypy.ini
       - run: poetry run mypy
   trial:
     needs: check_repo
diff --git a/.github/workflows/twisted_trunk.yml b/.github/workflows/twisted_trunk.yml
index 67ccc03f6e..7d629a4ed0 100644
--- a/.github/workflows/twisted_trunk.yml
+++ b/.github/workflows/twisted_trunk.yml
@@ -54,8 +54,8 @@ jobs:
           poetry remove twisted
           poetry add --extras tls git+https://github.com/twisted/twisted.git#${{ inputs.twisted_ref || 'trunk' }}
           poetry install --no-interaction --extras "all test"
-      - name: Remove warn_unused_ignores from mypy config
-        run: sed '/warn_unused_ignores = True/d' -i mypy.ini
+      - name: Remove unhelpful options from mypy config
+        run: sed -e '/warn_unused_ignores = True/d' -e '/warn_redundant_casts = True/d' -i mypy.ini
       - run: poetry run mypy
 
   trial:
diff --git a/CHANGES.md b/CHANGES.md
index a17734cfe3..01bec0fe46 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -1,3 +1,65 @@
+# Synapse 1.92.0rc1 (2023-09-05)
+
+### Features
+
+- Add configuration setting for CAS protocol version. Contributed by Aurélien Grimpard. ([\#15816](https://github.com/matrix-org/synapse/issues/15816))
+- Suppress notifications from message edits per [MSC3958](https://github.com/matrix-org/matrix-spec-proposals/pull/3958). ([\#16113](https://github.com/matrix-org/synapse/issues/16113))
+- Return a `Retry-After` with `M_LIMIT_EXCEEDED` error responses. ([\#16136](https://github.com/matrix-org/synapse/issues/16136))
+- Add `last_seen_ts` to the [admin users API](https://matrix-org.github.io/synapse/latest/admin_api/user_admin_api.html). ([\#16218](https://github.com/matrix-org/synapse/issues/16218))
+- Improve resource usage when sending data to a large number of remote hosts that are marked as "down". ([\#16223](https://github.com/matrix-org/synapse/issues/16223))
+
+### Bugfixes
+
+- Fix IPv6-related bugs on SMTP settings, adding groundwork to fix similar issues. Contributed by @evilham and @telmich (ungleich.ch). ([\#16155](https://github.com/matrix-org/synapse/issues/16155))
+- Fix a spec compliance issue where requests to the `/publicRooms` federation API would specify `include_all_networks` as a string. ([\#16185](https://github.com/matrix-org/synapse/issues/16185))
+- Fix inaccurate error message while attempting to ban or unban a user with the same or higher PL by spliting the conditional statements. Contributed by @leviosacz. ([\#16205](https://github.com/matrix-org/synapse/issues/16205))
+- Fix a rare bug that broke looping calls, which could lead to e.g. linearly increasing memory usage. Introduced in v1.90.0. ([\#16210](https://github.com/matrix-org/synapse/issues/16210))
+- Fix a long-standing bug where uploading images would fail if we could not generate thumbnails for them. ([\#16211](https://github.com/matrix-org/synapse/issues/16211))
+- Fix a long-standing bug where we did not correctly back off from servers that had "gone" if they returned 4xx series error codes. ([\#16221](https://github.com/matrix-org/synapse/issues/16221))
+
+### Improved Documentation
+
+- Update links to the [matrix.org blog](https://matrix.org/blog/). ([\#16008](https://github.com/matrix-org/synapse/issues/16008))
+- Document which [admin APIs](https://matrix-org.github.io/synapse/latest/usage/administration/admin_api/index.html) are disabled when experimental [MSC3861](https://github.com/matrix-org/matrix-spec-proposals/pull/3861) support is enabled. ([\#16168](https://github.com/matrix-org/synapse/issues/16168))
+- Document [`exclude_rooms_from_sync`](https://matrix-org.github.io/synapse/v1.92/usage/configuration/config_documentation.html#exclude_rooms_from_sync) configuration option. ([\#16178](https://github.com/matrix-org/synapse/issues/16178))
+
+### Internal Changes
+
+- Prepare unit tests for Python 3.12. ([\#16099](https://github.com/matrix-org/synapse/issues/16099))
+- Fix nightly CI jobs. ([\#16121](https://github.com/matrix-org/synapse/issues/16121), [\#16213](https://github.com/matrix-org/synapse/issues/16213))
+- Describe which rate limiter was hit in logs. ([\#16135](https://github.com/matrix-org/synapse/issues/16135))
+- Simplify presence code when using workers. ([\#16170](https://github.com/matrix-org/synapse/issues/16170))
+- Track per-device information in the presence code. ([\#16171](https://github.com/matrix-org/synapse/issues/16171), [\#16172](https://github.com/matrix-org/synapse/issues/16172))
+- Stop using the `event_txn_id` table. ([\#16175](https://github.com/matrix-org/synapse/issues/16175))
+- Use `AsyncMock` instead of custom code. ([\#16179](https://github.com/matrix-org/synapse/issues/16179), [\#16180](https://github.com/matrix-org/synapse/issues/16180))
+- Improve error reporting of invalid data passed to `/_matrix/key/v2/query`. ([\#16183](https://github.com/matrix-org/synapse/issues/16183))
+- Task scheduler: add replication notify for new task to launch ASAP. ([\#16184](https://github.com/matrix-org/synapse/issues/16184))
+- Improve type hints. ([\#16186](https://github.com/matrix-org/synapse/issues/16186), [\#16188](https://github.com/matrix-org/synapse/issues/16188), [\#16201](https://github.com/matrix-org/synapse/issues/16201))
+- Bump black version to 23.7.0. ([\#16187](https://github.com/matrix-org/synapse/issues/16187))
+- Log the details of background update failures. ([\#16212](https://github.com/matrix-org/synapse/issues/16212))
+- Cache device resync requests over replication. ([\#16241](https://github.com/matrix-org/synapse/issues/16241))
+
+### Updates to locked dependencies
+
+* Bump anyhow from 1.0.72 to 1.0.75. ([\#16141](https://github.com/matrix-org/synapse/issues/16141))
+* Bump furo from 2023.7.26 to 2023.8.19. ([\#16238](https://github.com/matrix-org/synapse/issues/16238))
+* Bump phonenumbers from 8.13.18 to 8.13.19. ([\#16237](https://github.com/matrix-org/synapse/issues/16237))
+* Bump psycopg2 from 2.9.6 to 2.9.7. ([\#16196](https://github.com/matrix-org/synapse/issues/16196))
+* Bump regex from 1.9.3 to 1.9.4. ([\#16195](https://github.com/matrix-org/synapse/issues/16195))
+* Bump ruff from 0.0.277 to 0.0.286. ([\#16198](https://github.com/matrix-org/synapse/issues/16198))
+* Bump sentry-sdk from 1.29.2 to 1.30.0. ([\#16236](https://github.com/matrix-org/synapse/issues/16236))
+* Bump serde from 1.0.184 to 1.0.188. ([\#16194](https://github.com/matrix-org/synapse/issues/16194))
+* Bump serde_json from 1.0.104 to 1.0.105. ([\#16140](https://github.com/matrix-org/synapse/issues/16140))
+* Bump types-psycopg2 from 2.9.21.10 to 2.9.21.11. ([\#16200](https://github.com/matrix-org/synapse/issues/16200))
+* Bump types-pyyaml from 6.0.12.10 to 6.0.12.11. ([\#16199](https://github.com/matrix-org/synapse/issues/16199))
+
+# Synapse 1.91.1 (2023-09-04)
+
+### Bugfixes
+
+- Fix a performance regression introduced in Synapse 1.91.0 where event persistence would cause an excessive linear growth in CPU usage. ([\#16220](https://github.com/matrix-org/synapse/issues/16220))
+
+
 # Synapse 1.91.0 (2023-08-30)
 
 No significant changes since 1.91.0rc1.
diff --git a/Cargo.lock b/Cargo.lock
index 61c0f1bd04..4d60f8dcb6 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -13,9 +13,9 @@ dependencies = [
 
 [[package]]
 name = "anyhow"
-version = "1.0.72"
+version = "1.0.75"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3b13c32d80ecc7ab747b80c3784bce54ee8a7a0cc4fbda9bf4cda2cf6fe90854"
+checksum = "a4668cab20f66d8d020e1fbc0ebe47217433c1b6c8f2040faf858554e394ace6"
 
 [[package]]
 name = "arc-swap"
@@ -291,9 +291,9 @@ dependencies = [
 
 [[package]]
 name = "regex"
-version = "1.9.3"
+version = "1.9.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "81bc1d4caf89fac26a70747fe603c130093b53c773888797a6329091246d651a"
+checksum = "12de2eff854e5fa4b1295edd650e227e9d8fb0c9e90b12e7f36d6a6811791a29"
 dependencies = [
  "aho-corasick",
  "memchr",
@@ -303,9 +303,9 @@ dependencies = [
 
 [[package]]
 name = "regex-automata"
-version = "0.3.6"
+version = "0.3.7"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "fed1ceff11a1dddaee50c9dc8e4938bd106e9d89ae372f192311e7da498e3b69"
+checksum = "49530408a136e16e5b486e883fbb6ba058e8e4e8ae6621a77b048b314336e629"
 dependencies = [
  "aho-corasick",
  "memchr",
@@ -314,9 +314,9 @@ dependencies = [
 
 [[package]]
 name = "regex-syntax"
-version = "0.7.4"
+version = "0.7.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e5ea92a5b6195c6ef2a0295ea818b312502c6fc94dde986c5553242e18fd4ce2"
+checksum = "dbb5fb1acd8a1a18b3dd5be62d25485eb770e05afb408a9627d14d451bae12da"
 
 [[package]]
 name = "ryu"
@@ -332,18 +332,18 @@ checksum = "d29ab0c6d3fc0ee92fe66e2d99f700eab17a8d57d1c1d3b748380fb20baa78cd"
 
 [[package]]
 name = "serde"
-version = "1.0.184"
+version = "1.0.188"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "2c911f4b04d7385c9035407a4eff5903bf4fe270fa046fda448b69e797f4fff0"
+checksum = "cf9e0fcba69a370eed61bcf2b728575f726b50b55cba78064753d708ddc7549e"
 dependencies = [
  "serde_derive",
 ]
 
 [[package]]
 name = "serde_derive"
-version = "1.0.184"
+version = "1.0.188"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "c1df27f5b29406ada06609b2e2f77fb34f6dbb104a457a671cc31dbed237e09e"
+checksum = "4eca7ac642d82aa35b60049a6eccb4be6be75e599bd2e9adb5f875a737654af2"
 dependencies = [
  "proc-macro2",
  "quote",
@@ -352,9 +352,9 @@ dependencies = [
 
 [[package]]
 name = "serde_json"
-version = "1.0.104"
+version = "1.0.105"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "076066c5f1078eac5b722a31827a8832fe108bed65dfa75e233c89f8206e976c"
+checksum = "693151e1ac27563d6dbcec9dee9fbd5da8539b20fa14ad3752b2e6d363ace360"
 dependencies = [
  "itoa",
  "ryu",
diff --git a/changelog.d/16220.bugfix b/changelog.d/16220.bugfix
deleted file mode 100644
index dcfac6bda1..0000000000
--- a/changelog.d/16220.bugfix
+++ /dev/null
@@ -1 +0,0 @@
-Fix a performance regression introduced in Synapse 1.91.0 where event persistence would cause excessive CPU usage over time.
diff --git a/debian/changelog b/debian/changelog
index 9c0f77e16a..2f870074e5 100644
--- a/debian/changelog
+++ b/debian/changelog
@@ -1,3 +1,15 @@
+matrix-synapse-py3 (1.92.0~rc1) stable; urgency=medium
+
+  * New Synapse release 1.92.0rc1.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 05 Sep 2023 11:21:43 +0100
+
+matrix-synapse-py3 (1.91.1) stable; urgency=medium
+
+  * New Synapse release 1.91.1.
+
+ -- Synapse Packaging team <packages@matrix.org>  Mon, 04 Sep 2023 14:03:18 +0100
+
 matrix-synapse-py3 (1.91.0) stable; urgency=medium
 
   * New Synapse release 1.91.0.
diff --git a/docs/admin_api/account_validity.md b/docs/admin_api/account_validity.md
index 87d8f7150e..dfa69e515b 100644
--- a/docs/admin_api/account_validity.md
+++ b/docs/admin_api/account_validity.md
@@ -1,5 +1,7 @@
 # Account validity API
 
+**Note:** This API is disabled when MSC3861 is enabled. [See #15582](https://github.com/matrix-org/synapse/pull/15582)
+
 This API allows a server administrator to manage the validity of an account. To
 use it, you must enable the account validity feature (under
 `account_validity`) in Synapse's configuration.
diff --git a/docs/admin_api/register_api.md b/docs/admin_api/register_api.md
index dd2830f3a1..e9a235ada5 100644
--- a/docs/admin_api/register_api.md
+++ b/docs/admin_api/register_api.md
@@ -1,5 +1,7 @@
 # Shared-Secret Registration
 
+**Note:** This API is disabled when MSC3861 is enabled. [See #15582](https://github.com/matrix-org/synapse/pull/15582)
+
 This API allows for the creation of users in an administrative and
 non-interactive way. This is generally used for bootstrapping a Synapse
 instance with administrator accounts.
diff --git a/docs/admin_api/user_admin_api.md b/docs/admin_api/user_admin_api.md
index 99abfea3a0..975a7a0da4 100644
--- a/docs/admin_api/user_admin_api.md
+++ b/docs/admin_api/user_admin_api.md
@@ -218,7 +218,7 @@ The following parameters should be set in the URL:
 - `name` - Is optional and filters to only return users with user ID localparts
   **or** displaynames that contain this value.
 - `guests` - string representing a bool - Is optional and if `false` will **exclude** guest users.
-  Defaults to `true` to include guest users.
+  Defaults to `true` to include guest users. This parameter is not supported when MSC3861 is enabled. [See #15582](https://github.com/matrix-org/synapse/pull/15582)
 - `admins` - Optional flag to filter admins. If `true`, only admins are queried. If `false`, admins are excluded from 
   the query. When the flag is absent (the default), **both** admins and non-admins are included in the search results.
 - `deactivated` - string representing a bool - Is optional and if `true` will **include** deactivated users.
@@ -242,6 +242,7 @@ The following parameters should be set in the URL:
   - `displayname` - Users are ordered alphabetically by `displayname`.
   - `avatar_url` - Users are ordered alphabetically by avatar URL.
   - `creation_ts` - Users are ordered by when the users was created in ms.
+  - `last_seen_ts` - Users are ordered by when the user was lastly seen in ms.
 
 - `dir` - Direction of media order. Either `f` for forwards or `b` for backwards.
   Setting this value to `b` will reverse the above sort order. Defaults to `f`.
@@ -272,6 +273,7 @@ The following fields are returned in the JSON response body:
   - `displayname` - string - The user's display name if they have set one.
   - `avatar_url` - string -  The user's avatar URL if they have set one.
   - `creation_ts` - integer - The user's creation timestamp in ms.
+  - `last_seen_ts` - integer - The user's last activity timestamp in ms.
 
 - `next_token`: string representing a positive integer - Indication for pagination. See above.
 - `total` - integer - Total number of media.
@@ -390,6 +392,8 @@ The following actions are **NOT** performed. The list may be incomplete.
 
 ## Reset password
 
+**Note:** This API is disabled when MSC3861 is enabled. [See #15582](https://github.com/matrix-org/synapse/pull/15582)
+
 Changes the password of another user. This will automatically log the user out of all their devices.
 
 The api is:
@@ -413,6 +417,8 @@ The parameter `logout_devices` is optional and defaults to `true`.
 
 ## Get whether a user is a server administrator or not
 
+**Note:** This API is disabled when MSC3861 is enabled. [See #15582](https://github.com/matrix-org/synapse/pull/15582)
+
 The api is:
 
 ```
@@ -430,6 +436,8 @@ A response body like the following is returned:
 
 ## Change whether a user is a server administrator or not
 
+**Note:** This API is disabled when MSC3861 is enabled. [See #15582](https://github.com/matrix-org/synapse/pull/15582)
+
 Note that you cannot demote yourself.
 
 The api is:
@@ -723,6 +731,8 @@ delete largest/smallest or newest/oldest files first.
 
 ## Login as a user
 
+**Note:** This API is disabled when MSC3861 is enabled. [See #15582](https://github.com/matrix-org/synapse/pull/15582)
+
 Get an access token that can be used to authenticate as that user. Useful for
 when admins wish to do actions on behalf of a user.
 
diff --git a/docs/development/releases.md b/docs/development/releases.md
index c9a8c69945..6e83c81e27 100644
--- a/docs/development/releases.md
+++ b/docs/development/releases.md
@@ -12,7 +12,7 @@ Note that this schedule might be modified depending on the availability of the
 Synapse team, e.g. releases may be skipped to avoid holidays.
 
 Release announcements can be found in the
-[release category of the Matrix blog](https://matrix.org/blog/category/releases).
+[release category of the Matrix blog](https://matrix.org/category/releases).
 
 ## Bugfix releases
 
@@ -34,4 +34,4 @@ be held to be released together.
 
 In some cases, a pre-disclosure of a security release will be issued as a notice
 to Synapse operators that there is an upcoming security release. These can be
-found in the [security category of the Matrix blog](https://matrix.org/blog/category/security).
+found in the [security category of the Matrix blog](https://matrix.org/category/security).
diff --git a/docs/usage/administration/admin_api/registration_tokens.md b/docs/usage/administration/admin_api/registration_tokens.md
index c5130859d4..ba95bcf038 100644
--- a/docs/usage/administration/admin_api/registration_tokens.md
+++ b/docs/usage/administration/admin_api/registration_tokens.md
@@ -1,5 +1,7 @@
 # Registration Tokens
 
+**Note:** This API is disabled when MSC3861 is enabled. [See #15582](https://github.com/matrix-org/synapse/pull/15582)
+
 This API allows you to manage tokens which can be used to authenticate
 registration requests, as proposed in
 [MSC3231](https://github.com/matrix-org/matrix-doc/blob/main/proposals/3231-token-authenticated-registration.md)
diff --git a/docs/usage/configuration/config_documentation.md b/docs/usage/configuration/config_documentation.md
index 743c51d76a..0b1725816e 100644
--- a/docs/usage/configuration/config_documentation.md
+++ b/docs/usage/configuration/config_documentation.md
@@ -3420,6 +3420,7 @@ Has the following sub-options:
    to style the login flow according to the identity provider in question.
    See the [spec](https://spec.matrix.org/latest/) for possible options here.
 * `server_url`: The URL of the CAS authorization endpoint.
+* `protocol_version`: The CAS protocol version, defaults to none (version 3 is required if you want to use "required_attributes").
 * `displayname_attribute`: The attribute of the CAS response to use as the display name.
    If no name is given here, no displayname will be set.
 * `required_attributes`:  It is possible to configure Synapse to only allow logins if CAS attributes
@@ -3433,6 +3434,7 @@ Example configuration:
 cas_config:
   enabled: true
   server_url: "https://cas-server.com"
+  protocol_version: 3
   displayname_attribute: name
   required_attributes:
     userGroup: "staff"
@@ -3865,6 +3867,19 @@ Example configuration:
 ```yaml
 forget_rooms_on_leave: false
 ```
+---
+### `exclude_rooms_from_sync`
+A list of rooms to exclude from sync responses. This is useful for server
+administrators wishing to group users into a room without these users being able
+to see it from their client.
+
+By default, no room is excluded.
+
+Example configuration:
+```yaml
+exclude_rooms_from_sync:
+    - !foo:example.com
+```
 
 ---
 ## Opentracing
diff --git a/mypy.ini b/mypy.ini
index 311a951aa8..fb5f44c939 100644
--- a/mypy.ini
+++ b/mypy.ini
@@ -87,18 +87,9 @@ ignore_missing_imports = True
 [mypy-saml2.*]
 ignore_missing_imports = True
 
-[mypy-service_identity.*]
-ignore_missing_imports = True
-
 [mypy-srvlookup.*]
 ignore_missing_imports = True
 
 # https://github.com/twisted/treq/pull/366
 [mypy-treq.*]
 ignore_missing_imports = True
-
-[mypy-incremental.*]
-ignore_missing_imports = True
-
-[mypy-setuptools_rust.*]
-ignore_missing_imports = True
diff --git a/poetry.lock b/poetry.lock
index e62c10da9f..1cefabb358 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -1,4 +1,4 @@
-# This file is automatically @generated by Poetry 1.5.1 and should not be changed by hand.
+# This file is automatically @generated by Poetry 1.6.1 and should not be changed by hand.
 
 [[package]]
 name = "alabaster"
@@ -148,36 +148,33 @@ lxml = ["lxml"]
 
 [[package]]
 name = "black"
-version = "23.3.0"
+version = "23.7.0"
 description = "The uncompromising code formatter."
 optional = false
-python-versions = ">=3.7"
+python-versions = ">=3.8"
 files = [
-    {file = "black-23.3.0-cp310-cp310-macosx_10_16_arm64.whl", hash = "sha256:0945e13506be58bf7db93ee5853243eb368ace1c08a24c65ce108986eac65915"},
-    {file = "black-23.3.0-cp310-cp310-macosx_10_16_universal2.whl", hash = "sha256:67de8d0c209eb5b330cce2469503de11bca4085880d62f1628bd9972cc3366b9"},
-    {file = "black-23.3.0-cp310-cp310-macosx_10_16_x86_64.whl", hash = "sha256:7c3eb7cea23904399866c55826b31c1f55bbcd3890ce22ff70466b907b6775c2"},
-    {file = "black-23.3.0-cp310-cp310-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:32daa9783106c28815d05b724238e30718f34155653d4d6e125dc7daec8e260c"},
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+mypy-extensions = ">=1.0.0"
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-typing-extensions = ">=3.10"
+typing-extensions = ">=4.1.0"
 
 [package.extras]
 dmypy = ["psutil (>=4.0)"]
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 "zope.schema" = "*"
 
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 python-versions = "*"
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 [[package]]
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 python-versions = ">=3.6"
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 optional = false
 python-versions = ">=3.7"
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-    {file = "ruff-0.0.277.tar.gz", hash = "sha256:2dab13cdedbf3af6d4427c07f47143746b6b95d9e4a254ac369a0edb9280a0d2"},
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+    {file = "ruff-0.0.286-py3-none-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:8301f0bb4ec1a5b29cfaf15b83565136c47abefb771603241af9d6038f8981e8"},
+    {file = "ruff-0.0.286-py3-none-manylinux_2_17_armv7l.manylinux2014_armv7l.whl", hash = "sha256:acc4598f810bbc465ce0ed84417ac687e392c993a84c7eaf3abf97638701c1ec"},
+    {file = "ruff-0.0.286-py3-none-manylinux_2_17_i686.manylinux2014_i686.whl", hash = "sha256:88c8e358b445eb66d47164fa38541cfcc267847d1e7a92dd186dddb1a0a9a17f"},
+    {file = "ruff-0.0.286-py3-none-manylinux_2_17_ppc64.manylinux2014_ppc64.whl", hash = "sha256:0433683d0c5dbcf6162a4beb2356e820a593243f1fa714072fec15e2e4f4c939"},
+    {file = "ruff-0.0.286-py3-none-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl", hash = "sha256:ddb61a0c4454cbe4623f4a07fef03c5ae921fe04fede8d15c6e36703c0a73b07"},
+    {file = "ruff-0.0.286-py3-none-manylinux_2_17_s390x.manylinux2014_s390x.whl", hash = "sha256:47549c7c0be24c8ae9f2bce6f1c49fbafea83bca80142d118306f08ec7414041"},
+    {file = "ruff-0.0.286-py3-none-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:559aa793149ac23dc4310f94f2c83209eedb16908a0343663be19bec42233d25"},
+    {file = "ruff-0.0.286-py3-none-musllinux_1_2_aarch64.whl", hash = "sha256:d73cfb1c3352e7aa0ce6fb2321f36fa1d4a2c48d2ceac694cb03611ddf0e4db6"},
+    {file = "ruff-0.0.286-py3-none-musllinux_1_2_armv7l.whl", hash = "sha256:3dad93b1f973c6d1db4b6a5da8690c5625a3fa32bdf38e543a6936e634b83dc3"},
+    {file = "ruff-0.0.286-py3-none-musllinux_1_2_i686.whl", hash = "sha256:26afc0851f4fc3738afcf30f5f8b8612a31ac3455cb76e611deea80f5c0bf3ce"},
+    {file = "ruff-0.0.286-py3-none-musllinux_1_2_x86_64.whl", hash = "sha256:9b6b116d1c4000de1b9bf027131dbc3b8a70507788f794c6b09509d28952c512"},
+    {file = "ruff-0.0.286-py3-none-win32.whl", hash = "sha256:556e965ac07c1e8c1c2d759ac512e526ecff62c00fde1a046acb088d3cbc1a6c"},
+    {file = "ruff-0.0.286-py3-none-win_amd64.whl", hash = "sha256:5d295c758961376c84aaa92d16e643d110be32add7465e197bfdaec5a431a107"},
+    {file = "ruff-0.0.286-py3-none-win_arm64.whl", hash = "sha256:1d6142d53ab7f164204b3133d053c4958d4d11ec3a39abf23a40b13b0784e3f0"},
+    {file = "ruff-0.0.286.tar.gz", hash = "sha256:f1e9d169cce81a384a26ee5bb8c919fe9ae88255f39a1a69fd1ebab233a85ed2"},
 ]
 
 [[package]]
@@ -2385,13 +2390,13 @@ doc = ["Sphinx", "sphinx-rtd-theme"]
 
 [[package]]
 name = "sentry-sdk"
-version = "1.29.2"
+version = "1.30.0"
 description = "Python client for Sentry (https://sentry.io)"
 optional = true
 python-versions = "*"
 files = [
-    {file = "sentry-sdk-1.29.2.tar.gz", hash = "sha256:a99ee105384788c3f228726a88baf515fe7b5f1d2d0f215a03d194369f158df7"},
-    {file = "sentry_sdk-1.29.2-py2.py3-none-any.whl", hash = "sha256:3e17215d8006612e2df02b0e73115eb8376c37e3f586d8436fa41644e605074d"},
+    {file = "sentry-sdk-1.30.0.tar.gz", hash = "sha256:7dc873b87e1faf4d00614afd1058bfa1522942f33daef8a59f90de8ed75cd10c"},
+    {file = "sentry_sdk-1.30.0-py2.py3-none-any.whl", hash = "sha256:2e53ad63f96bb9da6570ba2e755c267e529edcf58580a2c0d2a11ef26e1e678b"},
 ]
 
 [package.dependencies]
@@ -2414,6 +2419,7 @@ httpx = ["httpx (>=0.16.0)"]
 huey = ["huey (>=2)"]
 loguru = ["loguru (>=0.5)"]
 opentelemetry = ["opentelemetry-distro (>=0.35b0)"]
+opentelemetry-experimental = ["opentelemetry-distro (>=0.40b0,<1.0)", "opentelemetry-instrumentation-aiohttp-client (>=0.40b0,<1.0)", "opentelemetry-instrumentation-django (>=0.40b0,<1.0)", "opentelemetry-instrumentation-fastapi (>=0.40b0,<1.0)", "opentelemetry-instrumentation-flask (>=0.40b0,<1.0)", "opentelemetry-instrumentation-requests (>=0.40b0,<1.0)", "opentelemetry-instrumentation-sqlite3 (>=0.40b0,<1.0)", "opentelemetry-instrumentation-urllib (>=0.40b0,<1.0)"]
 pure-eval = ["asttokens", "executing", "pure-eval"]
 pymongo = ["pymongo (>=3.1)"]
 pyspark = ["pyspark (>=2.4.4)"]
@@ -2467,18 +2473,19 @@ testing-integration = ["build[virtualenv]", "filelock (>=3.4.0)", "jaraco.envs (
 
 [[package]]
 name = "setuptools-rust"
-version = "1.6.0"
+version = "1.7.0"
 description = "Setuptools Rust extension plugin"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "setuptools-rust-1.6.0.tar.gz", hash = "sha256:c86e734deac330597998bfbc08da45187e6b27837e23bd91eadb320732392262"},
-    {file = "setuptools_rust-1.6.0-py3-none-any.whl", hash = "sha256:e28ae09fb7167c44ab34434eb49279307d611547cb56cb9789955cdb54a1aed9"},
+    {file = "setuptools-rust-1.7.0.tar.gz", hash = "sha256:c7100999948235a38ae7e555fe199aa66c253dc384b125f5d85473bf81eae3a3"},
+    {file = "setuptools_rust-1.7.0-py3-none-any.whl", hash = "sha256:071099885949132a2180d16abf907b60837e74b4085047ba7e9c0f5b365310c1"},
 ]
 
 [package.dependencies]
 semantic-version = ">=2.8.2,<3"
 setuptools = ">=62.4"
+tomli = {version = ">=1.2.1", markers = "python_version < \"3.11\""}
 typing-extensions = ">=3.7.4.3"
 
 [[package]]
@@ -3002,13 +3009,13 @@ files = [
 
 [[package]]
 name = "types-psycopg2"
-version = "2.9.21.10"
+version = "2.9.21.11"
 description = "Typing stubs for psycopg2"
 optional = false
 python-versions = "*"
 files = [
-    {file = "types-psycopg2-2.9.21.10.tar.gz", hash = "sha256:c2600892312ae1c34e12f145749795d93dc4eac3ef7dbf8a9c1bfd45385e80d7"},
-    {file = "types_psycopg2-2.9.21.10-py3-none-any.whl", hash = "sha256:918224a0731a3650832e46633e720703b5beef7693a064e777d9748654fcf5e5"},
+    {file = "types-psycopg2-2.9.21.11.tar.gz", hash = "sha256:d5077eacf90e61db8c0b8eea2fdc9d4a97d7aaa16865fb4bd7034a7571520b4d"},
+    {file = "types_psycopg2-2.9.21.11-py3-none-any.whl", hash = "sha256:7a323d7744bc8a882fb5a6f63448e903fc70d3dc0d6da9ec1f9c6c4dc10a7102"},
 ]
 
 [[package]]
@@ -3027,13 +3034,13 @@ cryptography = ">=35.0.0"
 
 [[package]]
 name = "types-pyyaml"
-version = "6.0.12.10"
+version = "6.0.12.11"
 description = "Typing stubs for PyYAML"
 optional = false
 python-versions = "*"
 files = [
-    {file = "types-PyYAML-6.0.12.10.tar.gz", hash = "sha256:ebab3d0700b946553724ae6ca636ea932c1b0868701d4af121630e78d695fc97"},
-    {file = "types_PyYAML-6.0.12.10-py3-none-any.whl", hash = "sha256:662fa444963eff9b68120d70cda1af5a5f2aa57900003c2006d7626450eaae5f"},
+    {file = "types-PyYAML-6.0.12.11.tar.gz", hash = "sha256:7d340b19ca28cddfdba438ee638cd4084bde213e501a3978738543e27094775b"},
+    {file = "types_PyYAML-6.0.12.11-py3-none-any.whl", hash = "sha256:a461508f3096d1d5810ec5ab95d7eeecb651f3a15b71959999988942063bf01d"},
 ]
 
 [[package]]
@@ -3207,22 +3214,22 @@ files = [
 
 [[package]]
 name = "xmlschema"
-version = "2.2.2"
+version = "2.4.0"
 description = "An XML Schema validator and decoder"
 optional = true
 python-versions = ">=3.7"
 files = [
-    {file = "xmlschema-2.2.2-py3-none-any.whl", hash = "sha256:557f3632b54b6ff10576736bba62e43db84eb60f6465a83818576cd9ffcc1799"},
-    {file = "xmlschema-2.2.2.tar.gz", hash = "sha256:0caa96668807b4b51c42a0fe2b6610752bc59f069615df3e34dcfffb962973fd"},
+    {file = "xmlschema-2.4.0-py3-none-any.whl", hash = "sha256:dc87be0caaa61f42649899189aab2fd8e0d567f2cf548433ba7b79278d231a4a"},
+    {file = "xmlschema-2.4.0.tar.gz", hash = "sha256:d74cd0c10866ac609e1ef94a5a69b018ad16e39077bc6393408b40c6babee793"},
 ]
 
 [package.dependencies]
-elementpath = ">=4.0.0,<5.0.0"
+elementpath = ">=4.1.5,<5.0.0"
 
 [package.extras]
-codegen = ["elementpath (>=4.0.0,<5.0.0)", "jinja2"]
-dev = ["Sphinx", "coverage", "elementpath (>=4.0.0,<5.0.0)", "flake8", "jinja2", "lxml", "lxml-stubs", "memory-profiler", "mypy", "sphinx-rtd-theme", "tox"]
-docs = ["Sphinx", "elementpath (>=4.0.0,<5.0.0)", "jinja2", "sphinx-rtd-theme"]
+codegen = ["elementpath (>=4.1.5,<5.0.0)", "jinja2"]
+dev = ["Sphinx", "coverage", "elementpath (>=4.1.5,<5.0.0)", "flake8", "jinja2", "lxml", "lxml-stubs", "memory-profiler", "mypy", "sphinx-rtd-theme", "tox"]
+docs = ["Sphinx", "elementpath (>=4.1.5,<5.0.0)", "jinja2", "sphinx-rtd-theme"]
 
 [[package]]
 name = "zipp"
@@ -3343,4 +3350,4 @@ user-search = ["pyicu"]
 [metadata]
 lock-version = "2.0"
 python-versions = "^3.8.0"
-content-hash = "0a8c6605e7e1d0ac7188a5d02b47a029bfb0f917458b87cb40755911442383d8"
+content-hash = "4a3a82becd89b91e76e2bc2f8ba72123f665c517d9b841d9a34cd01b83a1adc3"
diff --git a/pyproject.toml b/pyproject.toml
index 2a4ff1ea01..c17f4da72d 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -35,7 +35,7 @@
         showcontent = true
 
 [tool.black]
-target-version = ['py37', 'py38', 'py39', 'py310']
+target-version = ['py38', 'py39', 'py310', 'py311']
 # black ignores everything in .gitignore by default, see
 # https://black.readthedocs.io/en/stable/usage_and_configuration/file_collection_and_discovery.html#gitignore
 # Use `extend-exclude` if you want to exclude something in addition to this.
@@ -89,7 +89,7 @@ manifest-path = "rust/Cargo.toml"
 
 [tool.poetry]
 name = "matrix-synapse"
-version = "1.91.0"
+version = "1.92.0rc1"
 description = "Homeserver for the Matrix decentralised comms protocol"
 authors = ["Matrix.org Team and Contributors <packages@matrix.org>"]
 license = "Apache-2.0"
@@ -306,10 +306,13 @@ all = [
 ]
 
 [tool.poetry.dev-dependencies]
-# We pin black so that our tests don't start failing on new releases.
+# We pin development dependencies in poetry.lock so that our tests don't start
+# failing on new releases. Keeping lower bounds loose here means that dependabot
+# can bump versions without having to update the content-hash in the lockfile.
+# This helps prevents merge conflicts when running a batch of dependabot updates.
 isort = ">=5.10.1"
-black = ">=22.3.0"
-ruff = "0.0.277"
+black = ">=22.7.0"
+ruff = "0.0.286"
 
 # Typechecking
 lxml-stubs = ">=0.4.0"
diff --git a/rust/benches/evaluator.rs b/rust/benches/evaluator.rs
index 6e1eab2a3b..14071105a0 100644
--- a/rust/benches/evaluator.rs
+++ b/rust/benches/evaluator.rs
@@ -197,7 +197,6 @@ fn bench_eval_message(b: &mut Bencher) {
         false,
         false,
         false,
-        false,
     );
 
     b.iter(|| eval.run(&rules, Some("bob"), Some("person")));
diff --git a/rust/src/push/base_rules.rs b/rust/src/push/base_rules.rs
index 00baceda91..59fd27665a 100644
--- a/rust/src/push/base_rules.rs
+++ b/rust/src/push/base_rules.rs
@@ -228,7 +228,7 @@ pub const BASE_APPEND_OVERRIDE_RULES: &[PushRule] = &[
     // We don't want to notify on edits *unless* the edit directly mentions a
     // user, which is handled above.
     PushRule {
-        rule_id: Cow::Borrowed("global/override/.org.matrix.msc3958.suppress_edits"),
+        rule_id: Cow::Borrowed("global/override/.m.rule.suppress_edits"),
         priority_class: 5,
         conditions: Cow::Borrowed(&[Condition::Known(KnownCondition::EventPropertyIs(
             EventPropertyIsCondition {
diff --git a/rust/src/push/evaluator.rs b/rust/src/push/evaluator.rs
index 48e670478b..5b9bf9b26a 100644
--- a/rust/src/push/evaluator.rs
+++ b/rust/src/push/evaluator.rs
@@ -564,7 +564,7 @@ fn test_requires_room_version_supports_condition() {
     };
     let rules = PushRules::new(vec![custom_rule]);
     result = evaluator.run(
-        &FilteredPushRules::py_new(rules, BTreeMap::new(), true, false, true, false),
+        &FilteredPushRules::py_new(rules, BTreeMap::new(), true, false, true),
         None,
         None,
     );
diff --git a/rust/src/push/mod.rs b/rust/src/push/mod.rs
index 829fb79d0e..8e91f506cc 100644
--- a/rust/src/push/mod.rs
+++ b/rust/src/push/mod.rs
@@ -527,7 +527,6 @@ pub struct FilteredPushRules {
     msc1767_enabled: bool,
     msc3381_polls_enabled: bool,
     msc3664_enabled: bool,
-    msc3958_suppress_edits_enabled: bool,
 }
 
 #[pymethods]
@@ -539,7 +538,6 @@ impl FilteredPushRules {
         msc1767_enabled: bool,
         msc3381_polls_enabled: bool,
         msc3664_enabled: bool,
-        msc3958_suppress_edits_enabled: bool,
     ) -> Self {
         Self {
             push_rules,
@@ -547,7 +545,6 @@ impl FilteredPushRules {
             msc1767_enabled,
             msc3381_polls_enabled,
             msc3664_enabled,
-            msc3958_suppress_edits_enabled,
         }
     }
 
@@ -584,12 +581,6 @@ impl FilteredPushRules {
                     return false;
                 }
 
-                if !self.msc3958_suppress_edits_enabled
-                    && rule.rule_id == "global/override/.org.matrix.msc3958.suppress_edits"
-                {
-                    return false;
-                }
-
                 true
             })
             .map(|r| {
diff --git a/stubs/synapse/synapse_rust/push.pyi b/stubs/synapse/synapse_rust/push.pyi
index d573a37b9a..1f432d4ecf 100644
--- a/stubs/synapse/synapse_rust/push.pyi
+++ b/stubs/synapse/synapse_rust/push.pyi
@@ -46,7 +46,6 @@ class FilteredPushRules:
         msc1767_enabled: bool,
         msc3381_polls_enabled: bool,
         msc3664_enabled: bool,
-        msc3958_suppress_edits_enabled: bool,
     ): ...
     def rules(self) -> Collection[Tuple[PushRule, bool]]: ...
 
diff --git a/synapse/__init__.py b/synapse/__init__.py
index 2f9c22a833..4a9bbc4d57 100644
--- a/synapse/__init__.py
+++ b/synapse/__init__.py
@@ -21,9 +21,14 @@ import os
 import sys
 from typing import Any, Dict
 
+from PIL import ImageFile
+
 from synapse.util.rust import check_rust_lib_up_to_date
 from synapse.util.stringutils import strtobool
 
+# Allow truncated JPEG images to be thumbnailed.
+ImageFile.LOAD_TRUNCATED_IMAGES = True
+
 # Check that we're not running on an unsupported Python version.
 #
 # Note that we use an (unneeded) variable here so that pyupgrade doesn't nuke the
diff --git a/synapse/_scripts/synapse_port_db.py b/synapse/_scripts/synapse_port_db.py
index 49242800b8..ab2b29cf1b 100755
--- a/synapse/_scripts/synapse_port_db.py
+++ b/synapse/_scripts/synapse_port_db.py
@@ -482,7 +482,10 @@ class Porter:
                         do_backward[0] = False
 
                 if forward_rows or backward_rows:
-                    headers = [column[0] for column in txn.description]
+                    assert txn.description is not None
+                    headers: Optional[List[str]] = [
+                        column[0] for column in txn.description
+                    ]
                 else:
                     headers = None
 
@@ -544,6 +547,7 @@ class Porter:
             def r(txn: LoggingTransaction) -> Tuple[List[str], List[Tuple]]:
                 txn.execute(select, (forward_chunk, self.batch_size))
                 rows = txn.fetchall()
+                assert txn.description is not None
                 headers = [column[0] for column in txn.description]
 
                 return headers, rows
@@ -919,7 +923,8 @@ class Porter:
         def r(txn: LoggingTransaction) -> Tuple[List[str], List[Tuple]]:
             txn.execute(select)
             rows = txn.fetchall()
-            headers: List[str] = [column[0] for column in txn.description]
+            assert txn.description is not None
+            headers = [column[0] for column in txn.description]
 
             ts_ind = headers.index("ts")
 
diff --git a/synapse/api/errors.py b/synapse/api/errors.py
index 7ffd72c42c..fdb2955be8 100644
--- a/synapse/api/errors.py
+++ b/synapse/api/errors.py
@@ -16,6 +16,7 @@
 """Contains exceptions and error codes."""
 
 import logging
+import math
 import typing
 from enum import Enum
 from http import HTTPStatus
@@ -210,6 +211,11 @@ class SynapseError(CodeMessageException):
     def error_dict(self, config: Optional["HomeServerConfig"]) -> "JsonDict":
         return cs_error(self.msg, self.errcode, **self._additional_fields)
 
+    @property
+    def debug_context(self) -> Optional[str]:
+        """Override this to add debugging context that shouldn't be sent to clients."""
+        return None
+
 
 class InvalidAPICallError(SynapseError):
     """You called an existing API endpoint, but fed that endpoint
@@ -503,19 +509,31 @@ class InvalidCaptchaError(SynapseError):
 class LimitExceededError(SynapseError):
     """A client has sent too many requests and is being throttled."""
 
+    include_retry_after_header = False
+
     def __init__(
         self,
+        limiter_name: str,
         code: int = 429,
-        msg: str = "Too Many Requests",
         retry_after_ms: Optional[int] = None,
         errcode: str = Codes.LIMIT_EXCEEDED,
     ):
-        super().__init__(code, msg, errcode)
+        headers = (
+            {"Retry-After": str(math.ceil(retry_after_ms / 1000))}
+            if self.include_retry_after_header and retry_after_ms is not None
+            else None
+        )
+        super().__init__(code, "Too Many Requests", errcode, headers=headers)
         self.retry_after_ms = retry_after_ms
+        self.limiter_name = limiter_name
 
     def error_dict(self, config: Optional["HomeServerConfig"]) -> "JsonDict":
         return cs_error(self.msg, self.errcode, retry_after_ms=self.retry_after_ms)
 
+    @property
+    def debug_context(self) -> Optional[str]:
+        return self.limiter_name
+
 
 class RoomKeysVersionError(SynapseError):
     """A client has tried to upload to a non-current version of the room_keys store"""
diff --git a/synapse/api/ratelimiting.py b/synapse/api/ratelimiting.py
index 511790c7c5..887b214d64 100644
--- a/synapse/api/ratelimiting.py
+++ b/synapse/api/ratelimiting.py
@@ -61,12 +61,16 @@ class Ratelimiter:
     """
 
     def __init__(
-        self, store: DataStore, clock: Clock, rate_hz: float, burst_count: int
+        self,
+        store: DataStore,
+        clock: Clock,
+        cfg: RatelimitSettings,
     ):
         self.clock = clock
-        self.rate_hz = rate_hz
-        self.burst_count = burst_count
+        self.rate_hz = cfg.per_second
+        self.burst_count = cfg.burst_count
         self.store = store
+        self._limiter_name = cfg.key
 
         # An ordered dictionary representing the token buckets tracked by this rate
         # limiter. Each entry maps a key of arbitrary type to a tuple representing:
@@ -305,7 +309,8 @@ class Ratelimiter:
 
         if not allowed:
             raise LimitExceededError(
-                retry_after_ms=int(1000 * (time_allowed - time_now_s))
+                limiter_name=self._limiter_name,
+                retry_after_ms=int(1000 * (time_allowed - time_now_s)),
             )
 
 
@@ -322,7 +327,9 @@ class RequestRatelimiter:
 
         # The rate_hz and burst_count are overridden on a per-user basis
         self.request_ratelimiter = Ratelimiter(
-            store=self.store, clock=self.clock, rate_hz=0, burst_count=0
+            store=self.store,
+            clock=self.clock,
+            cfg=RatelimitSettings(key=rc_message.key, per_second=0, burst_count=0),
         )
         self._rc_message = rc_message
 
@@ -332,8 +339,7 @@ class RequestRatelimiter:
             self.admin_redaction_ratelimiter: Optional[Ratelimiter] = Ratelimiter(
                 store=self.store,
                 clock=self.clock,
-                rate_hz=rc_admin_redaction.per_second,
-                burst_count=rc_admin_redaction.burst_count,
+                cfg=rc_admin_redaction,
             )
         else:
             self.admin_redaction_ratelimiter = None
diff --git a/synapse/config/_base.py b/synapse/config/_base.py
index 1d268a1817..69a8318127 100644
--- a/synapse/config/_base.py
+++ b/synapse/config/_base.py
@@ -186,9 +186,9 @@ class Config:
             TypeError, if given something other than an integer or a string
             ValueError: if given a string not of the form described above.
         """
-        if type(value) is int:
+        if type(value) is int:  # noqa: E721
             return value
-        elif type(value) is str:
+        elif isinstance(value, str):
             sizes = {"K": 1024, "M": 1024 * 1024}
             size = 1
             suffix = value[-1]
@@ -218,9 +218,9 @@ class Config:
             TypeError, if given something other than an integer or a string
             ValueError: if given a string not of the form described above.
         """
-        if type(value) is int:
+        if type(value) is int:  # noqa: E721
             return value
-        elif type(value) is str:
+        elif isinstance(value, str):
             second = 1000
             minute = 60 * second
             hour = 60 * minute
diff --git a/synapse/config/appservice.py b/synapse/config/appservice.py
index 919f81a9b7..a70dfbf41f 100644
--- a/synapse/config/appservice.py
+++ b/synapse/config/appservice.py
@@ -34,7 +34,7 @@ class AppServiceConfig(Config):
     def read_config(self, config: JsonDict, **kwargs: Any) -> None:
         self.app_service_config_files = config.get("app_service_config_files", [])
         if not isinstance(self.app_service_config_files, list) or not all(
-            type(x) is str for x in self.app_service_config_files
+            isinstance(x, str) for x in self.app_service_config_files
         ):
             raise ConfigError(
                 "Expected '%s' to be a list of AS config files:"
diff --git a/synapse/config/cas.py b/synapse/config/cas.py
index c4e63e7411..6e2d9addbf 100644
--- a/synapse/config/cas.py
+++ b/synapse/config/cas.py
@@ -18,7 +18,7 @@ from typing import Any, List
 from synapse.config.sso import SsoAttributeRequirement
 from synapse.types import JsonDict
 
-from ._base import Config
+from ._base import Config, ConfigError
 from ._util import validate_config
 
 
@@ -41,6 +41,16 @@ class CasConfig(Config):
             public_baseurl = self.root.server.public_baseurl
             self.cas_service_url = public_baseurl + "_matrix/client/r0/login/cas/ticket"
 
+            self.cas_protocol_version = cas_config.get("protocol_version")
+            if (
+                self.cas_protocol_version is not None
+                and self.cas_protocol_version not in [1, 2, 3]
+            ):
+                raise ConfigError(
+                    "Unsupported CAS protocol version %s (only versions 1, 2, 3 are supported)"
+                    % (self.cas_protocol_version,),
+                    ("cas_config", "protocol_version"),
+                )
             self.cas_displayname_attribute = cas_config.get("displayname_attribute")
             required_attributes = cas_config.get("required_attributes") or {}
             self.cas_required_attributes = _parsed_required_attributes_def(
@@ -54,6 +64,7 @@ class CasConfig(Config):
         else:
             self.cas_server_url = None
             self.cas_service_url = None
+            self.cas_protocol_version = None
             self.cas_displayname_attribute = None
             self.cas_required_attributes = []
 
diff --git a/synapse/config/experimental.py b/synapse/config/experimental.py
index 277ea4675b..cabe0d4397 100644
--- a/synapse/config/experimental.py
+++ b/synapse/config/experimental.py
@@ -18,6 +18,7 @@ from typing import TYPE_CHECKING, Any, Optional
 import attr
 import attr.validators
 
+from synapse.api.errors import LimitExceededError
 from synapse.api.room_versions import KNOWN_ROOM_VERSIONS, RoomVersions
 from synapse.config import ConfigError
 from synapse.config._base import Config, RootConfig
@@ -383,11 +384,6 @@ class ExperimentalConfig(Config):
         # MSC3391: Removing account data.
         self.msc3391_enabled = experimental.get("msc3391_enabled", False)
 
-        # MSC3959: Do not generate notifications for edits.
-        self.msc3958_supress_edit_notifs = experimental.get(
-            "msc3958_supress_edit_notifs", False
-        )
-
         # MSC3967: Do not require UIA when first uploading cross signing keys
         self.msc3967_enabled = experimental.get("msc3967_enabled", False)
 
@@ -411,3 +407,11 @@ class ExperimentalConfig(Config):
         self.msc4010_push_rules_account_data = experimental.get(
             "msc4010_push_rules_account_data", False
         )
+
+        # MSC4041: Use HTTP header Retry-After to enable library-assisted retry handling
+        #
+        # This is a bit hacky, but the most reasonable way to *alway* include the
+        # headers.
+        LimitExceededError.include_retry_after_header = experimental.get(
+            "msc4041_enabled", False
+        )
diff --git a/synapse/config/ratelimiting.py b/synapse/config/ratelimiting.py
index a5514e70a2..4efbaeac0d 100644
--- a/synapse/config/ratelimiting.py
+++ b/synapse/config/ratelimiting.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
-from typing import Any, Dict, Optional
+from typing import Any, Dict, Optional, cast
 
 import attr
 
@@ -21,16 +21,47 @@ from synapse.types import JsonDict
 from ._base import Config
 
 
+@attr.s(slots=True, frozen=True, auto_attribs=True)
 class RatelimitSettings:
-    def __init__(
-        self,
-        config: Dict[str, float],
+    key: str
+    per_second: float
+    burst_count: int
+
+    @classmethod
+    def parse(
+        cls,
+        config: Dict[str, Any],
+        key: str,
         defaults: Optional[Dict[str, float]] = None,
-    ):
+    ) -> "RatelimitSettings":
+        """Parse config[key] as a new-style rate limiter config.
+
+        The key may refer to a nested dictionary using a full stop (.) to separate
+        each nested key. For example, use the key "a.b.c" to parse the following:
+
+        a:
+          b:
+            c:
+              per_second: 10
+              burst_count: 200
+
+        If this lookup fails, we'll fallback to the defaults.
+        """
         defaults = defaults or {"per_second": 0.17, "burst_count": 3.0}
 
-        self.per_second = config.get("per_second", defaults["per_second"])
-        self.burst_count = int(config.get("burst_count", defaults["burst_count"]))
+        rl_config = config
+        for part in key.split("."):
+            rl_config = rl_config.get(part, {})
+
+        # By this point we should have hit the rate limiter parameters.
+        # We don't actually check this though!
+        rl_config = cast(Dict[str, float], rl_config)
+
+        return cls(
+            key=key,
+            per_second=rl_config.get("per_second", defaults["per_second"]),
+            burst_count=int(rl_config.get("burst_count", defaults["burst_count"])),
+        )
 
 
 @attr.s(auto_attribs=True)
@@ -49,15 +80,14 @@ class RatelimitConfig(Config):
         # Load the new-style messages config if it exists. Otherwise fall back
         # to the old method.
         if "rc_message" in config:
-            self.rc_message = RatelimitSettings(
-                config["rc_message"], defaults={"per_second": 0.2, "burst_count": 10.0}
+            self.rc_message = RatelimitSettings.parse(
+                config, "rc_message", defaults={"per_second": 0.2, "burst_count": 10.0}
             )
         else:
             self.rc_message = RatelimitSettings(
-                {
-                    "per_second": config.get("rc_messages_per_second", 0.2),
-                    "burst_count": config.get("rc_message_burst_count", 10.0),
-                }
+                key="rc_messages",
+                per_second=config.get("rc_messages_per_second", 0.2),
+                burst_count=config.get("rc_message_burst_count", 10.0),
             )
 
         # Load the new-style federation config, if it exists. Otherwise, fall
@@ -79,51 +109,59 @@ class RatelimitConfig(Config):
                 }
             )
 
-        self.rc_registration = RatelimitSettings(config.get("rc_registration", {}))
+        self.rc_registration = RatelimitSettings.parse(config, "rc_registration", {})
 
-        self.rc_registration_token_validity = RatelimitSettings(
-            config.get("rc_registration_token_validity", {}),
+        self.rc_registration_token_validity = RatelimitSettings.parse(
+            config,
+            "rc_registration_token_validity",
             defaults={"per_second": 0.1, "burst_count": 5},
         )
 
         # It is reasonable to login with a bunch of devices at once (i.e. when
         # setting up an account), but it is *not* valid to continually be
         # logging into new devices.
-        rc_login_config = config.get("rc_login", {})
-        self.rc_login_address = RatelimitSettings(
-            rc_login_config.get("address", {}),
+        self.rc_login_address = RatelimitSettings.parse(
+            config,
+            "rc_login.address",
             defaults={"per_second": 0.003, "burst_count": 5},
         )
-        self.rc_login_account = RatelimitSettings(
-            rc_login_config.get("account", {}),
+        self.rc_login_account = RatelimitSettings.parse(
+            config,
+            "rc_login.account",
             defaults={"per_second": 0.003, "burst_count": 5},
         )
-        self.rc_login_failed_attempts = RatelimitSettings(
-            rc_login_config.get("failed_attempts", {})
+        self.rc_login_failed_attempts = RatelimitSettings.parse(
+            config,
+            "rc_login.failed_attempts",
+            {},
         )
 
         self.federation_rr_transactions_per_room_per_second = config.get(
             "federation_rr_transactions_per_room_per_second", 50
         )
 
-        rc_admin_redaction = config.get("rc_admin_redaction")
         self.rc_admin_redaction = None
-        if rc_admin_redaction:
-            self.rc_admin_redaction = RatelimitSettings(rc_admin_redaction)
+        if "rc_admin_redaction" in config:
+            self.rc_admin_redaction = RatelimitSettings.parse(
+                config, "rc_admin_redaction", {}
+            )
 
-        self.rc_joins_local = RatelimitSettings(
-            config.get("rc_joins", {}).get("local", {}),
+        self.rc_joins_local = RatelimitSettings.parse(
+            config,
+            "rc_joins.local",
             defaults={"per_second": 0.1, "burst_count": 10},
         )
-        self.rc_joins_remote = RatelimitSettings(
-            config.get("rc_joins", {}).get("remote", {}),
+        self.rc_joins_remote = RatelimitSettings.parse(
+            config,
+            "rc_joins.remote",
             defaults={"per_second": 0.01, "burst_count": 10},
         )
 
         # Track the rate of joins to a given room. If there are too many, temporarily
         # prevent local joins and remote joins via this server.
-        self.rc_joins_per_room = RatelimitSettings(
-            config.get("rc_joins_per_room", {}),
+        self.rc_joins_per_room = RatelimitSettings.parse(
+            config,
+            "rc_joins_per_room",
             defaults={"per_second": 1, "burst_count": 10},
         )
 
@@ -132,31 +170,37 @@ class RatelimitConfig(Config):
         # * For requests received over federation this is keyed by the origin.
         #
         # Note that this isn't exposed in the configuration as it is obscure.
-        self.rc_key_requests = RatelimitSettings(
-            config.get("rc_key_requests", {}),
+        self.rc_key_requests = RatelimitSettings.parse(
+            config,
+            "rc_key_requests",
             defaults={"per_second": 20, "burst_count": 100},
         )
 
-        self.rc_3pid_validation = RatelimitSettings(
-            config.get("rc_3pid_validation") or {},
+        self.rc_3pid_validation = RatelimitSettings.parse(
+            config,
+            "rc_3pid_validation",
             defaults={"per_second": 0.003, "burst_count": 5},
         )
 
-        self.rc_invites_per_room = RatelimitSettings(
-            config.get("rc_invites", {}).get("per_room", {}),
+        self.rc_invites_per_room = RatelimitSettings.parse(
+            config,
+            "rc_invites.per_room",
             defaults={"per_second": 0.3, "burst_count": 10},
         )
-        self.rc_invites_per_user = RatelimitSettings(
-            config.get("rc_invites", {}).get("per_user", {}),
+        self.rc_invites_per_user = RatelimitSettings.parse(
+            config,
+            "rc_invites.per_user",
             defaults={"per_second": 0.003, "burst_count": 5},
         )
 
-        self.rc_invites_per_issuer = RatelimitSettings(
-            config.get("rc_invites", {}).get("per_issuer", {}),
+        self.rc_invites_per_issuer = RatelimitSettings.parse(
+            config,
+            "rc_invites.per_issuer",
             defaults={"per_second": 0.3, "burst_count": 10},
         )
 
-        self.rc_third_party_invite = RatelimitSettings(
-            config.get("rc_third_party_invite", {}),
+        self.rc_third_party_invite = RatelimitSettings.parse(
+            config,
+            "rc_third_party_invite",
             defaults={"per_second": 0.0025, "burst_count": 5},
         )
diff --git a/synapse/event_auth.py b/synapse/event_auth.py
index 3a260a492b..2ac9f8b309 100644
--- a/synapse/event_auth.py
+++ b/synapse/event_auth.py
@@ -669,12 +669,18 @@ def _is_membership_change_allowed(
                     errcode=Codes.INSUFFICIENT_POWER,
                 )
     elif Membership.BAN == membership:
-        if user_level < ban_level or user_level <= target_level:
+        if user_level < ban_level:
             raise UnstableSpecAuthError(
                 403,
                 "You don't have permission to ban",
                 errcode=Codes.INSUFFICIENT_POWER,
             )
+        elif user_level <= target_level:
+            raise UnstableSpecAuthError(
+                403,
+                "You don't have permission to ban this user",
+                errcode=Codes.INSUFFICIENT_POWER,
+            )
     elif room_version.knock_join_rule and Membership.KNOCK == membership:
         if join_rule != JoinRules.KNOCK and (
             not room_version.knock_restricted_join_rule
@@ -846,11 +852,11 @@ def _check_power_levels(
                 "kick",
                 "invite",
             }:
-                if type(v) is not int:
+                if type(v) is not int:  # noqa: E721
                     raise SynapseError(400, f"{v!r} must be an integer.")
             if k in {"events", "notifications", "users"}:
                 if not isinstance(v, collections.abc.Mapping) or not all(
-                    type(v) is int for v in v.values()
+                    type(v) is int for v in v.values()  # noqa: E721
                 ):
                     raise SynapseError(
                         400,
diff --git a/synapse/events/utils.py b/synapse/events/utils.py
index 52acb21955..53af423a5a 100644
--- a/synapse/events/utils.py
+++ b/synapse/events/utils.py
@@ -702,7 +702,7 @@ def _copy_power_level_value_as_integer(
     :raises TypeError: if `old_value` is neither an integer nor a base-10 string
         representation of an integer.
     """
-    if type(old_value) is int:
+    if type(old_value) is int:  # noqa: E721
         power_levels[key] = old_value
         return
 
@@ -730,7 +730,7 @@ def validate_canonicaljson(value: Any) -> None:
     * Floats
     * NaN, Infinity, -Infinity
     """
-    if type(value) is int:
+    if type(value) is int:  # noqa: E721
         if value < CANONICALJSON_MIN_INT or CANONICALJSON_MAX_INT < value:
             raise SynapseError(400, "JSON integer out of range", Codes.BAD_JSON)
 
diff --git a/synapse/events/validator.py b/synapse/events/validator.py
index 9278f1a1aa..34625dd7a1 100644
--- a/synapse/events/validator.py
+++ b/synapse/events/validator.py
@@ -151,7 +151,7 @@ class EventValidator:
         max_lifetime = event.content.get("max_lifetime")
 
         if min_lifetime is not None:
-            if type(min_lifetime) is not int:
+            if type(min_lifetime) is not int:  # noqa: E721
                 raise SynapseError(
                     code=400,
                     msg="'min_lifetime' must be an integer",
@@ -159,7 +159,7 @@ class EventValidator:
                 )
 
         if max_lifetime is not None:
-            if type(max_lifetime) is not int:
+            if type(max_lifetime) is not int:  # noqa: E721
                 raise SynapseError(
                     code=400,
                     msg="'max_lifetime' must be an integer",
diff --git a/synapse/federation/federation_base.py b/synapse/federation/federation_base.py
index 31e0260b83..d4e7dd45a9 100644
--- a/synapse/federation/federation_base.py
+++ b/synapse/federation/federation_base.py
@@ -280,7 +280,7 @@ def event_from_pdu_json(pdu_json: JsonDict, room_version: RoomVersion) -> EventB
         _strip_unsigned_values(pdu_json)
 
     depth = pdu_json["depth"]
-    if type(depth) is not int:
+    if type(depth) is not int:  # noqa: E721
         raise SynapseError(400, "Depth %r not an intger" % (depth,), Codes.BAD_JSON)
 
     if depth < 0:
diff --git a/synapse/federation/federation_client.py b/synapse/federation/federation_client.py
index 89bd597409..607013f121 100644
--- a/synapse/federation/federation_client.py
+++ b/synapse/federation/federation_client.py
@@ -1891,7 +1891,7 @@ class TimestampToEventResponse:
             )
 
         origin_server_ts = d.get("origin_server_ts")
-        if type(origin_server_ts) is not int:
+        if type(origin_server_ts) is not int:  # noqa: E721
             raise ValueError(
                 "Invalid response: 'origin_server_ts' must be a int but received %r"
                 % origin_server_ts
diff --git a/synapse/federation/send_queue.py b/synapse/federation/send_queue.py
index fb448f2155..6520795635 100644
--- a/synapse/federation/send_queue.py
+++ b/synapse/federation/send_queue.py
@@ -49,7 +49,7 @@ from synapse.api.presence import UserPresenceState
 from synapse.federation.sender import AbstractFederationSender, FederationSender
 from synapse.metrics import LaterGauge
 from synapse.replication.tcp.streams.federation import FederationStream
-from synapse.types import JsonDict, ReadReceipt, RoomStreamToken
+from synapse.types import JsonDict, ReadReceipt, RoomStreamToken, StrCollection
 from synapse.util.metrics import Measure
 
 from .units import Edu
@@ -229,7 +229,7 @@ class FederationRemoteSendQueue(AbstractFederationSender):
         """
         # nothing to do here: the replication listener will handle it.
 
-    def send_presence_to_destinations(
+    async def send_presence_to_destinations(
         self, states: Iterable[UserPresenceState], destinations: Iterable[str]
     ) -> None:
         """As per FederationSender
@@ -245,7 +245,9 @@ class FederationRemoteSendQueue(AbstractFederationSender):
 
         self.notifier.on_new_replication_data()
 
-    def send_device_messages(self, destination: str, immediate: bool = True) -> None:
+    async def send_device_messages(
+        self, destinations: StrCollection, immediate: bool = True
+    ) -> None:
         """As per FederationSender"""
         # We don't need to replicate this as it gets sent down a different
         # stream.
@@ -463,7 +465,7 @@ class ParsedFederationStreamData:
     edus: Dict[str, List[Edu]]
 
 
-def process_rows_for_federation(
+async def process_rows_for_federation(
     transaction_queue: FederationSender,
     rows: List[FederationStream.FederationStreamRow],
 ) -> None:
@@ -496,7 +498,7 @@ def process_rows_for_federation(
         parsed_row.add_to_buffer(buff)
 
     for state, destinations in buff.presence_destinations:
-        transaction_queue.send_presence_to_destinations(
+        await transaction_queue.send_presence_to_destinations(
             states=[state], destinations=destinations
         )
 
diff --git a/synapse/federation/sender/__init__.py b/synapse/federation/sender/__init__.py
index 97abbdee18..fb20fd8a10 100644
--- a/synapse/federation/sender/__init__.py
+++ b/synapse/federation/sender/__init__.py
@@ -147,7 +147,10 @@ from twisted.internet import defer
 import synapse.metrics
 from synapse.api.presence import UserPresenceState
 from synapse.events import EventBase
-from synapse.federation.sender.per_destination_queue import PerDestinationQueue
+from synapse.federation.sender.per_destination_queue import (
+    CATCHUP_RETRY_INTERVAL,
+    PerDestinationQueue,
+)
 from synapse.federation.sender.transaction_manager import TransactionManager
 from synapse.federation.units import Edu
 from synapse.logging.context import make_deferred_yieldable, run_in_background
@@ -161,9 +164,10 @@ from synapse.metrics.background_process_metrics import (
     run_as_background_process,
     wrap_as_background_process,
 )
-from synapse.types import JsonDict, ReadReceipt, RoomStreamToken
+from synapse.types import JsonDict, ReadReceipt, RoomStreamToken, StrCollection
 from synapse.util import Clock
 from synapse.util.metrics import Measure
+from synapse.util.retryutils import filter_destinations_by_retry_limiter
 
 if TYPE_CHECKING:
     from synapse.events.presence_router import PresenceRouter
@@ -213,7 +217,7 @@ class AbstractFederationSender(metaclass=abc.ABCMeta):
         raise NotImplementedError()
 
     @abc.abstractmethod
-    def send_presence_to_destinations(
+    async def send_presence_to_destinations(
         self, states: Iterable[UserPresenceState], destinations: Iterable[str]
     ) -> None:
         """Send the given presence states to the given destinations.
@@ -242,9 +246,11 @@ class AbstractFederationSender(metaclass=abc.ABCMeta):
         raise NotImplementedError()
 
     @abc.abstractmethod
-    def send_device_messages(self, destination: str, immediate: bool = True) -> None:
+    async def send_device_messages(
+        self, destinations: StrCollection, immediate: bool = True
+    ) -> None:
         """Tells the sender that a new device message is ready to be sent to the
-        destination. The `immediate` flag specifies whether the messages should
+        destinations. The `immediate` flag specifies whether the messages should
         be tried to be sent immediately, or whether it can be delayed for a
         short while (to aid performance).
         """
@@ -716,6 +722,13 @@ class FederationSender(AbstractFederationSender):
             pdu.internal_metadata.stream_ordering,
         )
 
+        destinations = await filter_destinations_by_retry_limiter(
+            destinations,
+            clock=self.clock,
+            store=self.store,
+            retry_due_within_ms=CATCHUP_RETRY_INTERVAL,
+        )
+
         for destination in destinations:
             self._get_per_destination_queue(destination).send_pdu(pdu)
 
@@ -763,12 +776,20 @@ class FederationSender(AbstractFederationSender):
         domains_set = await self._storage_controllers.state.get_current_hosts_in_room_or_partial_state_approximation(
             room_id
         )
-        domains = [
+        domains: StrCollection = [
             d
             for d in domains_set
             if not self.is_mine_server_name(d)
             and self._federation_shard_config.should_handle(self._instance_name, d)
         ]
+
+        domains = await filter_destinations_by_retry_limiter(
+            domains,
+            clock=self.clock,
+            store=self.store,
+            retry_due_within_ms=CATCHUP_RETRY_INTERVAL,
+        )
+
         if not domains:
             return
 
@@ -816,7 +837,7 @@ class FederationSender(AbstractFederationSender):
         for queue in queues:
             queue.flush_read_receipts_for_room(room_id)
 
-    def send_presence_to_destinations(
+    async def send_presence_to_destinations(
         self, states: Iterable[UserPresenceState], destinations: Iterable[str]
     ) -> None:
         """Send the given presence states to the given destinations.
@@ -831,13 +852,20 @@ class FederationSender(AbstractFederationSender):
         for state in states:
             assert self.is_mine_id(state.user_id)
 
+        destinations = await filter_destinations_by_retry_limiter(
+            [
+                d
+                for d in destinations
+                if self._federation_shard_config.should_handle(self._instance_name, d)
+            ],
+            clock=self.clock,
+            store=self.store,
+            retry_due_within_ms=CATCHUP_RETRY_INTERVAL,
+        )
+
         for destination in destinations:
             if self.is_mine_server_name(destination):
                 continue
-            if not self._federation_shard_config.should_handle(
-                self._instance_name, destination
-            ):
-                continue
 
             self._get_per_destination_queue(destination).send_presence(
                 states, start_loop=False
@@ -896,21 +924,29 @@ class FederationSender(AbstractFederationSender):
         else:
             queue.send_edu(edu)
 
-    def send_device_messages(self, destination: str, immediate: bool = True) -> None:
-        if self.is_mine_server_name(destination):
-            logger.warning("Not sending device update to ourselves")
-            return
+    async def send_device_messages(
+        self, destinations: StrCollection, immediate: bool = True
+    ) -> None:
+        destinations = await filter_destinations_by_retry_limiter(
+            [
+                destination
+                for destination in destinations
+                if self._federation_shard_config.should_handle(
+                    self._instance_name, destination
+                )
+                and not self.is_mine_server_name(destination)
+            ],
+            clock=self.clock,
+            store=self.store,
+            retry_due_within_ms=CATCHUP_RETRY_INTERVAL,
+        )
 
-        if not self._federation_shard_config.should_handle(
-            self._instance_name, destination
-        ):
-            return
-
-        if immediate:
-            self._get_per_destination_queue(destination).attempt_new_transaction()
-        else:
-            self._get_per_destination_queue(destination).mark_new_data()
-            self._destination_wakeup_queue.add_to_queue(destination)
+        for destination in destinations:
+            if immediate:
+                self._get_per_destination_queue(destination).attempt_new_transaction()
+            else:
+                self._get_per_destination_queue(destination).mark_new_data()
+                self._destination_wakeup_queue.add_to_queue(destination)
 
     def wake_destination(self, destination: str) -> None:
         """Called when we want to retry sending transactions to a remote.
diff --git a/synapse/federation/sender/per_destination_queue.py b/synapse/federation/sender/per_destination_queue.py
index 31c5c2b7de..9105ba664c 100644
--- a/synapse/federation/sender/per_destination_queue.py
+++ b/synapse/federation/sender/per_destination_queue.py
@@ -59,6 +59,10 @@ sent_edus_by_type = Counter(
 )
 
 
+# If the retry interval is larger than this then we enter "catchup" mode
+CATCHUP_RETRY_INTERVAL = 60 * 60 * 1000
+
+
 class PerDestinationQueue:
     """
     Manages the per-destination transmission queues.
@@ -370,7 +374,7 @@ class PerDestinationQueue:
                 ),
             )
 
-            if e.retry_interval > 60 * 60 * 1000:
+            if e.retry_interval > CATCHUP_RETRY_INTERVAL:
                 # we won't retry for another hour!
                 # (this suggests a significant outage)
                 # We drop pending EDUs because otherwise they will
diff --git a/synapse/federation/transport/client.py b/synapse/federation/transport/client.py
index 0afa1a3514..37903a79ec 100644
--- a/synapse/federation/transport/client.py
+++ b/synapse/federation/transport/client.py
@@ -249,8 +249,10 @@ class TransportLayerClient:
             data=json_data,
             json_data_callback=json_data_callback,
             long_retries=True,
-            backoff_on_404=True,  # If we get a 404 the other side has gone
             try_trailing_slash_on_400=True,
+            # Sending a transaction should always succeed, if it doesn't
+            # then something is wrong and we should backoff.
+            backoff_on_all_error_codes=True,
         )
 
     async def make_query(
@@ -475,13 +477,11 @@ class TransportLayerClient:
         See synapse.federation.federation_client.FederationClient.get_public_rooms for
         more information.
         """
+        path = _create_v1_path("/publicRooms")
+
         if search_filter:
             # this uses MSC2197 (Search Filtering over Federation)
-            path = _create_v1_path("/publicRooms")
-
-            data: Dict[str, Any] = {
-                "include_all_networks": "true" if include_all_networks else "false"
-            }
+            data: Dict[str, Any] = {"include_all_networks": include_all_networks}
             if third_party_instance_id:
                 data["third_party_instance_id"] = third_party_instance_id
             if limit:
@@ -505,17 +505,15 @@ class TransportLayerClient:
                     )
                 raise
         else:
-            path = _create_v1_path("/publicRooms")
-
             args: Dict[str, Union[str, Iterable[str]]] = {
                 "include_all_networks": "true" if include_all_networks else "false"
             }
             if third_party_instance_id:
-                args["third_party_instance_id"] = (third_party_instance_id,)
+                args["third_party_instance_id"] = third_party_instance_id
             if limit:
-                args["limit"] = [str(limit)]
+                args["limit"] = str(limit)
             if since_token:
-                args["since"] = [since_token]
+                args["since"] = since_token
 
             try:
                 response = await self.client.get_json(
diff --git a/synapse/handlers/admin.py b/synapse/handlers/admin.py
index 0e812a6d8b..2f0e5f3b0a 100644
--- a/synapse/handlers/admin.py
+++ b/synapse/handlers/admin.py
@@ -76,6 +76,7 @@ class AdminHandler:
             "consent_ts",
             "user_type",
             "is_guest",
+            "last_seen_ts",
         }
 
         if self._msc3866_enabled:
diff --git a/synapse/handlers/auth.py b/synapse/handlers/auth.py
index 59ecafa6a0..2b0c505130 100644
--- a/synapse/handlers/auth.py
+++ b/synapse/handlers/auth.py
@@ -218,19 +218,17 @@ class AuthHandler:
         self._failed_uia_attempts_ratelimiter = Ratelimiter(
             store=self.store,
             clock=self.clock,
-            rate_hz=self.hs.config.ratelimiting.rc_login_failed_attempts.per_second,
-            burst_count=self.hs.config.ratelimiting.rc_login_failed_attempts.burst_count,
+            cfg=self.hs.config.ratelimiting.rc_login_failed_attempts,
         )
 
         # The number of seconds to keep a UI auth session active.
         self._ui_auth_session_timeout = hs.config.auth.ui_auth_session_timeout
 
-        # Ratelimitier for failed /login attempts
+        # Ratelimiter for failed /login attempts
         self._failed_login_attempts_ratelimiter = Ratelimiter(
             store=self.store,
             clock=hs.get_clock(),
-            rate_hz=self.hs.config.ratelimiting.rc_login_failed_attempts.per_second,
-            burst_count=self.hs.config.ratelimiting.rc_login_failed_attempts.burst_count,
+            cfg=self.hs.config.ratelimiting.rc_login_failed_attempts,
         )
 
         self._clock = self.hs.get_clock()
diff --git a/synapse/handlers/cas.py b/synapse/handlers/cas.py
index 5c71637038..a850545453 100644
--- a/synapse/handlers/cas.py
+++ b/synapse/handlers/cas.py
@@ -67,6 +67,7 @@ class CasHandler:
 
         self._cas_server_url = hs.config.cas.cas_server_url
         self._cas_service_url = hs.config.cas.cas_service_url
+        self._cas_protocol_version = hs.config.cas.cas_protocol_version
         self._cas_displayname_attribute = hs.config.cas.cas_displayname_attribute
         self._cas_required_attributes = hs.config.cas.cas_required_attributes
 
@@ -121,7 +122,10 @@ class CasHandler:
         Returns:
             The parsed CAS response.
         """
-        uri = self._cas_server_url + "/proxyValidate"
+        if self._cas_protocol_version == 3:
+            uri = self._cas_server_url + "/p3/proxyValidate"
+        else:
+            uri = self._cas_server_url + "/proxyValidate"
         args = {
             "ticket": ticket,
             "service": self._build_service_param(service_args),
diff --git a/synapse/handlers/device.py b/synapse/handlers/device.py
index 5ae427d52c..763f56dfc1 100644
--- a/synapse/handlers/device.py
+++ b/synapse/handlers/device.py
@@ -836,17 +836,16 @@ class DeviceHandler(DeviceWorkerHandler):
                             user_id,
                             hosts,
                         )
-                        for host in hosts:
-                            self.federation_sender.send_device_messages(
-                                host, immediate=False
-                            )
-                            # TODO: when called, this isn't in a logging context.
-                            # This leads to log spam, sentry event spam, and massive
-                            # memory usage.
-                            # See https://github.com/matrix-org/synapse/issues/12552.
-                            # log_kv(
-                            #     {"message": "sent device update to host", "host": host}
-                            # )
+                        await self.federation_sender.send_device_messages(
+                            hosts, immediate=False
+                        )
+                        # TODO: when called, this isn't in a logging context.
+                        # This leads to log spam, sentry event spam, and massive
+                        # memory usage.
+                        # See https://github.com/matrix-org/synapse/issues/12552.
+                        # log_kv(
+                        #     {"message": "sent device update to host", "host": host}
+                        # )
 
                     if current_stream_id != stream_id:
                         # Clear the set of hosts we've already sent to as we're
@@ -951,8 +950,9 @@ class DeviceHandler(DeviceWorkerHandler):
 
         # Notify things that device lists need to be sent out.
         self.notifier.notify_replication()
-        for host in potentially_changed_hosts:
-            self.federation_sender.send_device_messages(host, immediate=False)
+        await self.federation_sender.send_device_messages(
+            potentially_changed_hosts, immediate=False
+        )
 
 
 def _update_device_from_client_ips(
diff --git a/synapse/handlers/devicemessage.py b/synapse/handlers/devicemessage.py
index 17ff8821d9..1c79f7a61e 100644
--- a/synapse/handlers/devicemessage.py
+++ b/synapse/handlers/devicemessage.py
@@ -90,8 +90,7 @@ class DeviceMessageHandler:
         self._ratelimiter = Ratelimiter(
             store=self.store,
             clock=hs.get_clock(),
-            rate_hz=hs.config.ratelimiting.rc_key_requests.per_second,
-            burst_count=hs.config.ratelimiting.rc_key_requests.burst_count,
+            cfg=hs.config.ratelimiting.rc_key_requests,
         )
 
     async def on_direct_to_device_edu(self, origin: str, content: JsonDict) -> None:
@@ -303,10 +302,9 @@ class DeviceMessageHandler:
         )
 
         if self.federation_sender:
-            for destination in remote_messages.keys():
-                # Enqueue a new federation transaction to send the new
-                # device messages to each remote destination.
-                self.federation_sender.send_device_messages(destination)
+            # Enqueue a new federation transaction to send the new
+            # device messages to each remote destination.
+            await self.federation_sender.send_device_messages(remote_messages.keys())
 
     async def get_events_for_dehydrated_device(
         self,
diff --git a/synapse/handlers/events.py b/synapse/handlers/events.py
index 33359f6ed7..d12803bf0f 100644
--- a/synapse/handlers/events.py
+++ b/synapse/handlers/events.py
@@ -67,6 +67,7 @@ class EventStreamHandler:
 
         context = await presence_handler.user_syncing(
             requester.user.to_string(),
+            requester.device_id,
             affect_presence=affect_presence,
             presence_state=PresenceState.ONLINE,
         )
diff --git a/synapse/handlers/identity.py b/synapse/handlers/identity.py
index 3031384d25..472879c964 100644
--- a/synapse/handlers/identity.py
+++ b/synapse/handlers/identity.py
@@ -66,14 +66,12 @@ class IdentityHandler:
         self._3pid_validation_ratelimiter_ip = Ratelimiter(
             store=self.store,
             clock=hs.get_clock(),
-            rate_hz=hs.config.ratelimiting.rc_3pid_validation.per_second,
-            burst_count=hs.config.ratelimiting.rc_3pid_validation.burst_count,
+            cfg=hs.config.ratelimiting.rc_3pid_validation,
         )
         self._3pid_validation_ratelimiter_address = Ratelimiter(
             store=self.store,
             clock=hs.get_clock(),
-            rate_hz=hs.config.ratelimiting.rc_3pid_validation.per_second,
-            burst_count=hs.config.ratelimiting.rc_3pid_validation.burst_count,
+            cfg=hs.config.ratelimiting.rc_3pid_validation,
         )
 
     async def ratelimit_request_token_requests(
diff --git a/synapse/handlers/message.py b/synapse/handlers/message.py
index a74db1dccf..d6be18cdef 100644
--- a/synapse/handlers/message.py
+++ b/synapse/handlers/message.py
@@ -379,7 +379,7 @@ class MessageHandler:
         """
 
         expiry_ts = event.content.get(EventContentFields.SELF_DESTRUCT_AFTER)
-        if type(expiry_ts) is not int or event.is_state():
+        if type(expiry_ts) is not int or event.is_state():  # noqa: E721
             return
 
         # _schedule_expiry_for_event won't actually schedule anything if there's already
@@ -908,19 +908,6 @@ class EventCreationHandler:
             if existing_event_id:
                 return existing_event_id
 
-        # Some requsters don't have device IDs (appservice, guests, and access
-        # tokens minted with the admin API), fallback to checking the access token
-        # ID, which should be close enough.
-        if requester.access_token_id:
-            existing_event_id = (
-                await self.store.get_event_id_from_transaction_id_and_token_id(
-                    room_id,
-                    requester.user.to_string(),
-                    requester.access_token_id,
-                    txn_id,
-                )
-            )
-
         return existing_event_id
 
     async def get_event_from_transaction(
@@ -1474,23 +1461,23 @@ class EventCreationHandler:
 
         # We now persist the event (and update the cache in parallel, since we
         # don't want to block on it).
-        event, context = events_and_context[0]
+        #
+        # Note: mypy gets confused if we inline dl and check with twisted#11770.
+        # Some kind of bug in mypy's deduction?
+        deferreds = (
+            run_in_background(
+                self._persist_events,
+                requester=requester,
+                events_and_context=events_and_context,
+                ratelimit=ratelimit,
+                extra_users=extra_users,
+            ),
+            run_in_background(
+                self.cache_joined_hosts_for_events, events_and_context
+            ).addErrback(log_failure, "cache_joined_hosts_for_event failed"),
+        )
         result, _ = await make_deferred_yieldable(
-            gather_results(
-                (
-                    run_in_background(
-                        self._persist_events,
-                        requester=requester,
-                        events_and_context=events_and_context,
-                        ratelimit=ratelimit,
-                        extra_users=extra_users,
-                    ),
-                    run_in_background(
-                        self.cache_joined_hosts_for_events, events_and_context
-                    ).addErrback(log_failure, "cache_joined_hosts_for_event failed"),
-                ),
-                consumeErrors=True,
-            )
+            gather_results(deferreds, consumeErrors=True)
         ).addErrback(unwrapFirstError)
 
         return result
@@ -1921,7 +1908,10 @@ class EventCreationHandler:
                 # We don't want to block sending messages on any presence code. This
                 # matters as sometimes presence code can take a while.
                 run_as_background_process(
-                    "bump_presence_active_time", self._bump_active_time, requester.user
+                    "bump_presence_active_time",
+                    self._bump_active_time,
+                    requester.user,
+                    requester.device_id,
                 )
 
         async def _notify() -> None:
@@ -1958,10 +1948,10 @@ class EventCreationHandler:
         logger.info("maybe_kick_guest_users %r", current_state)
         await self.hs.get_room_member_handler().kick_guest_users(current_state)
 
-    async def _bump_active_time(self, user: UserID) -> None:
+    async def _bump_active_time(self, user: UserID, device_id: Optional[str]) -> None:
         try:
             presence = self.hs.get_presence_handler()
-            await presence.bump_presence_active_time(user)
+            await presence.bump_presence_active_time(user, device_id)
         except Exception:
             logger.exception("Error bumping presence active time")
 
diff --git a/synapse/handlers/presence.py b/synapse/handlers/presence.py
index e8e9db4b91..f31e18328b 100644
--- a/synapse/handlers/presence.py
+++ b/synapse/handlers/presence.py
@@ -23,6 +23,7 @@ The methods that define policy are:
 """
 import abc
 import contextlib
+import itertools
 import logging
 from bisect import bisect
 from contextlib import contextmanager
@@ -151,15 +152,13 @@ class BasePresenceHandler(abc.ABC):
 
         self._federation_queue = PresenceFederationQueue(hs, self)
 
-        self._busy_presence_enabled = hs.config.experimental.msc3026_enabled
-
         self.VALID_PRESENCE: Tuple[str, ...] = (
             PresenceState.ONLINE,
             PresenceState.UNAVAILABLE,
             PresenceState.OFFLINE,
         )
 
-        if self._busy_presence_enabled:
+        if hs.config.experimental.msc3026_enabled:
             self.VALID_PRESENCE += (PresenceState.BUSY,)
 
         active_presence = self.store.take_presence_startup_info()
@@ -167,7 +166,11 @@ class BasePresenceHandler(abc.ABC):
 
     @abc.abstractmethod
     async def user_syncing(
-        self, user_id: str, affect_presence: bool, presence_state: str
+        self,
+        user_id: str,
+        device_id: Optional[str],
+        affect_presence: bool,
+        presence_state: str,
     ) -> ContextManager[None]:
         """Returns a context manager that should surround any stream requests
         from the user.
@@ -178,6 +181,7 @@ class BasePresenceHandler(abc.ABC):
 
         Args:
             user_id: the user that is starting a sync
+            device_id: the user's device that is starting a sync
             affect_presence: If false this function will be a no-op.
                 Useful for streams that are not associated with an actual
                 client that is being used by a user.
@@ -185,15 +189,17 @@ class BasePresenceHandler(abc.ABC):
         """
 
     @abc.abstractmethod
-    def get_currently_syncing_users_for_replication(self) -> Iterable[str]:
-        """Get an iterable of syncing users on this worker, to send to the presence handler
+    def get_currently_syncing_users_for_replication(
+        self,
+    ) -> Iterable[Tuple[str, Optional[str]]]:
+        """Get an iterable of syncing users and devices on this worker, to send to the presence handler
 
         This is called when a replication connection is established. It should return
-        a list of user ids, which are then sent as USER_SYNC commands to inform the
-        process handling presence about those users.
+        a list of tuples of user ID & device ID, which are then sent as USER_SYNC commands
+        to inform the process handling presence about those users/devices.
 
         Returns:
-            An iterable of user_id strings.
+            An iterable of tuples of user ID and device ID.
         """
 
     async def get_state(self, target_user: UserID) -> UserPresenceState:
@@ -254,28 +260,39 @@ class BasePresenceHandler(abc.ABC):
     async def set_state(
         self,
         target_user: UserID,
+        device_id: Optional[str],
         state: JsonDict,
-        ignore_status_msg: bool = False,
         force_notify: bool = False,
+        is_sync: bool = False,
     ) -> None:
         """Set the presence state of the user.
 
         Args:
             target_user: The ID of the user to set the presence state of.
+            device_id: the device that the user is setting the presence state of.
             state: The presence state as a JSON dictionary.
-            ignore_status_msg: True to ignore the "status_msg" field of the `state` dict.
-                If False, the user's current status will be updated.
             force_notify: Whether to force notification of the update to clients.
+            is_sync: True if this update was from a sync, which results in
+                *not* overriding a previously set BUSY status, updating the
+                user's last_user_sync_ts, and ignoring the "status_msg" field of
+                the `state` dict.
         """
 
     @abc.abstractmethod
-    async def bump_presence_active_time(self, user: UserID) -> None:
+    async def bump_presence_active_time(
+        self, user: UserID, device_id: Optional[str]
+    ) -> None:
         """We've seen the user do something that indicates they're interacting
         with the app.
         """
 
     async def update_external_syncs_row(  # noqa: B027 (no-op by design)
-        self, process_id: str, user_id: str, is_syncing: bool, sync_time_msec: int
+        self,
+        process_id: str,
+        user_id: str,
+        device_id: Optional[str],
+        is_syncing: bool,
+        sync_time_msec: int,
     ) -> None:
         """Update the syncing users for an external process as a delta.
 
@@ -286,6 +303,7 @@ class BasePresenceHandler(abc.ABC):
                 syncing against. This allows synapse to process updates
                 as user start and stop syncing against a given process.
             user_id: The user who has started or stopped syncing
+            device_id: The user's device that has started or stopped syncing
             is_syncing: Whether or not the user is now syncing
             sync_time_msec: Time in ms when the user was last syncing
         """
@@ -336,7 +354,9 @@ class BasePresenceHandler(abc.ABC):
         )
 
         for destination, host_states in hosts_to_states.items():
-            self._federation.send_presence_to_destinations(host_states, [destination])
+            await self._federation.send_presence_to_destinations(
+                host_states, [destination]
+            )
 
     async def send_full_presence_to_users(self, user_ids: StrCollection) -> None:
         """
@@ -381,7 +401,9 @@ class BasePresenceHandler(abc.ABC):
         # We set force_notify=True here so that this presence update is guaranteed to
         # increment the presence stream ID (which resending the current user's presence
         # otherwise would not do).
-        await self.set_state(UserID.from_string(user_id), state, force_notify=True)
+        await self.set_state(
+            UserID.from_string(user_id), None, state, force_notify=True
+        )
 
     async def is_visible(self, observed_user: UserID, observer_user: UserID) -> bool:
         raise NotImplementedError(
@@ -414,16 +436,18 @@ class WorkerPresenceHandler(BasePresenceHandler):
             hs.config.worker.writers.presence,
         )
 
-        # The number of ongoing syncs on this process, by user id.
+        # The number of ongoing syncs on this process, by (user ID, device ID).
         # Empty if _presence_enabled is false.
-        self._user_to_num_current_syncs: Dict[str, int] = {}
+        self._user_device_to_num_current_syncs: Dict[
+            Tuple[str, Optional[str]], int
+        ] = {}
 
         self.notifier = hs.get_notifier()
         self.instance_id = hs.get_instance_id()
 
-        # user_id -> last_sync_ms. Lists the users that have stopped syncing but
-        # we haven't notified the presence writer of that yet
-        self.users_going_offline: Dict[str, int] = {}
+        # (user_id, device_id) -> last_sync_ms. Lists the devices that have stopped
+        # syncing but we haven't notified the presence writer of that yet
+        self._user_devices_going_offline: Dict[Tuple[str, Optional[str]], int] = {}
 
         self._bump_active_client = ReplicationBumpPresenceActiveTime.make_client(hs)
         self._set_state_client = ReplicationPresenceSetState.make_client(hs)
@@ -446,42 +470,54 @@ class WorkerPresenceHandler(BasePresenceHandler):
                 ClearUserSyncsCommand(self.instance_id)
             )
 
-    def send_user_sync(self, user_id: str, is_syncing: bool, last_sync_ms: int) -> None:
+    def send_user_sync(
+        self,
+        user_id: str,
+        device_id: Optional[str],
+        is_syncing: bool,
+        last_sync_ms: int,
+    ) -> None:
         if self._presence_enabled:
             self.hs.get_replication_command_handler().send_user_sync(
-                self.instance_id, user_id, is_syncing, last_sync_ms
+                self.instance_id, user_id, device_id, is_syncing, last_sync_ms
             )
 
-    def mark_as_coming_online(self, user_id: str) -> None:
+    def mark_as_coming_online(self, user_id: str, device_id: Optional[str]) -> None:
         """A user has started syncing. Send a UserSync to the presence writer,
         unless they had recently stopped syncing.
         """
-        going_offline = self.users_going_offline.pop(user_id, None)
+        going_offline = self._user_devices_going_offline.pop((user_id, device_id), None)
         if not going_offline:
             # Safe to skip because we haven't yet told the presence writer they
             # were offline
-            self.send_user_sync(user_id, True, self.clock.time_msec())
+            self.send_user_sync(user_id, device_id, True, self.clock.time_msec())
 
-    def mark_as_going_offline(self, user_id: str) -> None:
+    def mark_as_going_offline(self, user_id: str, device_id: Optional[str]) -> None:
         """A user has stopped syncing. We wait before notifying the presence
         writer as its likely they'll come back soon. This allows us to avoid
         sending a stopped syncing immediately followed by a started syncing
         notification to the presence writer
         """
-        self.users_going_offline[user_id] = self.clock.time_msec()
+        self._user_devices_going_offline[(user_id, device_id)] = self.clock.time_msec()
 
     def send_stop_syncing(self) -> None:
         """Check if there are any users who have stopped syncing a while ago and
         haven't come back yet. If there are poke the presence writer about them.
         """
         now = self.clock.time_msec()
-        for user_id, last_sync_ms in list(self.users_going_offline.items()):
+        for (user_id, device_id), last_sync_ms in list(
+            self._user_devices_going_offline.items()
+        ):
             if now - last_sync_ms > UPDATE_SYNCING_USERS_MS:
-                self.users_going_offline.pop(user_id, None)
-                self.send_user_sync(user_id, False, last_sync_ms)
+                self._user_devices_going_offline.pop((user_id, device_id), None)
+                self.send_user_sync(user_id, device_id, False, last_sync_ms)
 
     async def user_syncing(
-        self, user_id: str, affect_presence: bool, presence_state: str
+        self,
+        user_id: str,
+        device_id: Optional[str],
+        affect_presence: bool,
+        presence_state: str,
     ) -> ContextManager[None]:
         """Record that a user is syncing.
 
@@ -491,36 +527,32 @@ class WorkerPresenceHandler(BasePresenceHandler):
         if not affect_presence or not self._presence_enabled:
             return _NullContextManager()
 
-        prev_state = await self.current_state_for_user(user_id)
-        if prev_state.state != PresenceState.BUSY:
-            # We set state here but pass ignore_status_msg = True as we don't want to
-            # cause the status message to be cleared.
-            # Note that this causes last_active_ts to be incremented which is not
-            # what the spec wants: see comment in the BasePresenceHandler version
-            # of this function.
-            await self.set_state(
-                UserID.from_string(user_id),
-                {"presence": presence_state},
-                ignore_status_msg=True,
-            )
+        # Note that this causes last_active_ts to be incremented which is not
+        # what the spec wants.
+        await self.set_state(
+            UserID.from_string(user_id),
+            device_id,
+            state={"presence": presence_state},
+            is_sync=True,
+        )
 
-        curr_sync = self._user_to_num_current_syncs.get(user_id, 0)
-        self._user_to_num_current_syncs[user_id] = curr_sync + 1
+        curr_sync = self._user_device_to_num_current_syncs.get((user_id, device_id), 0)
+        self._user_device_to_num_current_syncs[(user_id, device_id)] = curr_sync + 1
 
-        # If we went from no in flight sync to some, notify replication
-        if self._user_to_num_current_syncs[user_id] == 1:
-            self.mark_as_coming_online(user_id)
+        # If this is the first in-flight sync, notify replication
+        if self._user_device_to_num_current_syncs[(user_id, device_id)] == 1:
+            self.mark_as_coming_online(user_id, device_id)
 
         def _end() -> None:
             # We check that the user_id is in user_to_num_current_syncs because
             # user_to_num_current_syncs may have been cleared if we are
             # shutting down.
-            if user_id in self._user_to_num_current_syncs:
-                self._user_to_num_current_syncs[user_id] -= 1
+            if (user_id, device_id) in self._user_device_to_num_current_syncs:
+                self._user_device_to_num_current_syncs[(user_id, device_id)] -= 1
 
-                # If we went from one in flight sync to non, notify replication
-                if self._user_to_num_current_syncs[user_id] == 0:
-                    self.mark_as_going_offline(user_id)
+                # If there are no more in-flight syncs, notify replication
+                if self._user_device_to_num_current_syncs[(user_id, device_id)] == 0:
+                    self.mark_as_going_offline(user_id, device_id)
 
         @contextlib.contextmanager
         def _user_syncing() -> Generator[None, None, None]:
@@ -587,28 +619,34 @@ class WorkerPresenceHandler(BasePresenceHandler):
         # If this is a federation sender, notify about presence updates.
         await self.maybe_send_presence_to_interested_destinations(state_to_notify)
 
-    def get_currently_syncing_users_for_replication(self) -> Iterable[str]:
+    def get_currently_syncing_users_for_replication(
+        self,
+    ) -> Iterable[Tuple[str, Optional[str]]]:
         return [
-            user_id
-            for user_id, count in self._user_to_num_current_syncs.items()
+            user_id_device_id
+            for user_id_device_id, count in self._user_device_to_num_current_syncs.items()
             if count > 0
         ]
 
     async def set_state(
         self,
         target_user: UserID,
+        device_id: Optional[str],
         state: JsonDict,
-        ignore_status_msg: bool = False,
         force_notify: bool = False,
+        is_sync: bool = False,
     ) -> None:
         """Set the presence state of the user.
 
         Args:
             target_user: The ID of the user to set the presence state of.
+            device_id: the device that the user is setting the presence state of.
             state: The presence state as a JSON dictionary.
-            ignore_status_msg: True to ignore the "status_msg" field of the `state` dict.
-                If False, the user's current status will be updated.
             force_notify: Whether to force notification of the update to clients.
+            is_sync: True if this update was from a sync, which results in
+                *not* overriding a previously set BUSY status, updating the
+                user's last_user_sync_ts, and ignoring the "status_msg" field of
+                the `state` dict.
         """
         presence = state["presence"]
 
@@ -625,12 +663,15 @@ class WorkerPresenceHandler(BasePresenceHandler):
         await self._set_state_client(
             instance_name=self._presence_writer_instance,
             user_id=user_id,
+            device_id=device_id,
             state=state,
-            ignore_status_msg=ignore_status_msg,
             force_notify=force_notify,
+            is_sync=is_sync,
         )
 
-    async def bump_presence_active_time(self, user: UserID) -> None:
+    async def bump_presence_active_time(
+        self, user: UserID, device_id: Optional[str]
+    ) -> None:
         """We've seen the user do something that indicates they're interacting
         with the app.
         """
@@ -641,7 +682,9 @@ class WorkerPresenceHandler(BasePresenceHandler):
         # Proxy request to instance that writes presence
         user_id = user.to_string()
         await self._bump_active_client(
-            instance_name=self._presence_writer_instance, user_id=user_id
+            instance_name=self._presence_writer_instance,
+            user_id=user_id,
+            device_id=device_id,
         )
 
 
@@ -703,17 +746,23 @@ class PresenceHandler(BasePresenceHandler):
 
         # Keeps track of the number of *ongoing* syncs on this process. While
         # this is non zero a user will never go offline.
-        self.user_to_num_current_syncs: Dict[str, int] = {}
+        self._user_device_to_num_current_syncs: Dict[
+            Tuple[str, Optional[str]], int
+        ] = {}
 
         # Keeps track of the number of *ongoing* syncs on other processes.
+        #
         # While any sync is ongoing on another process the user will never
         # go offline.
+        #
         # Each process has a unique identifier and an update frequency. If
         # no update is received from that process within the update period then
         # we assume that all the sync requests on that process have stopped.
-        # Stored as a dict from process_id to set of user_id, and a dict of
-        # process_id to millisecond timestamp last updated.
-        self.external_process_to_current_syncs: Dict[str, Set[str]] = {}
+        # Stored as a dict from process_id to set of (user_id, device_id), and
+        # a dict of process_id to millisecond timestamp last updated.
+        self.external_process_to_current_syncs: Dict[
+            str, Set[Tuple[str, Optional[str]]]
+        ] = {}
         self.external_process_last_updated_ms: Dict[str, int] = {}
 
         self.external_sync_linearizer = Linearizer(name="external_sync_linearizer")
@@ -889,7 +938,7 @@ class PresenceHandler(BasePresenceHandler):
                 )
 
                 for destination, states in hosts_to_states.items():
-                    self._federation_queue.send_presence_to_destinations(
+                    await self._federation_queue.send_presence_to_destinations(
                         states, [destination]
                     )
 
@@ -918,7 +967,10 @@ class PresenceHandler(BasePresenceHandler):
             # that were syncing on that process to see if they need to be timed
             # out.
             users_to_check.update(
-                self.external_process_to_current_syncs.pop(process_id, ())
+                user_id
+                for user_id, device_id in self.external_process_to_current_syncs.pop(
+                    process_id, ()
+                )
             )
             self.external_process_last_updated_ms.pop(process_id)
 
@@ -931,11 +983,15 @@ class PresenceHandler(BasePresenceHandler):
 
         syncing_user_ids = {
             user_id
-            for user_id, count in self.user_to_num_current_syncs.items()
+            for (user_id, _), count in self._user_device_to_num_current_syncs.items()
             if count
         }
-        for user_ids in self.external_process_to_current_syncs.values():
-            syncing_user_ids.update(user_ids)
+        syncing_user_ids.update(
+            user_id
+            for user_id, _ in itertools.chain(
+                *self.external_process_to_current_syncs.values()
+            )
+        )
 
         changes = handle_timeouts(
             states,
@@ -946,7 +1002,9 @@ class PresenceHandler(BasePresenceHandler):
 
         return await self._update_states(changes)
 
-    async def bump_presence_active_time(self, user: UserID) -> None:
+    async def bump_presence_active_time(
+        self, user: UserID, device_id: Optional[str]
+    ) -> None:
         """We've seen the user do something that indicates they're interacting
         with the app.
         """
@@ -969,6 +1027,7 @@ class PresenceHandler(BasePresenceHandler):
     async def user_syncing(
         self,
         user_id: str,
+        device_id: Optional[str],
         affect_presence: bool = True,
         presence_state: str = PresenceState.ONLINE,
     ) -> ContextManager[None]:
@@ -980,7 +1039,8 @@ class PresenceHandler(BasePresenceHandler):
         when users disconnect/reconnect.
 
         Args:
-            user_id
+            user_id: the user that is starting a sync
+            device_id: the user's device that is starting a sync
             affect_presence: If false this function will be a no-op.
                 Useful for streams that are not associated with an actual
                 client that is being used by a user.
@@ -989,52 +1049,21 @@ class PresenceHandler(BasePresenceHandler):
         if not affect_presence or not self._presence_enabled:
             return _NullContextManager()
 
-        curr_sync = self.user_to_num_current_syncs.get(user_id, 0)
-        self.user_to_num_current_syncs[user_id] = curr_sync + 1
+        curr_sync = self._user_device_to_num_current_syncs.get((user_id, device_id), 0)
+        self._user_device_to_num_current_syncs[(user_id, device_id)] = curr_sync + 1
 
-        prev_state = await self.current_state_for_user(user_id)
-
-        # If they're busy then they don't stop being busy just by syncing,
-        # so just update the last sync time.
-        if prev_state.state != PresenceState.BUSY:
-            # XXX: We set_state separately here and just update the last_active_ts above
-            # This keeps the logic as similar as possible between the worker and single
-            # process modes. Using set_state will actually cause last_active_ts to be
-            # updated always, which is not what the spec calls for, but synapse has done
-            # this for... forever, I think.
-            await self.set_state(
-                UserID.from_string(user_id),
-                {"presence": presence_state},
-                ignore_status_msg=True,
-            )
-            # Retrieve the new state for the logic below. This should come from the
-            # in-memory cache.
-            prev_state = await self.current_state_for_user(user_id)
-
-        # To keep the single process behaviour consistent with worker mode, run the
-        # same logic as `update_external_syncs_row`, even though it looks weird.
-        if prev_state.state == PresenceState.OFFLINE:
-            await self._update_states(
-                [
-                    prev_state.copy_and_replace(
-                        state=PresenceState.ONLINE,
-                        last_active_ts=self.clock.time_msec(),
-                        last_user_sync_ts=self.clock.time_msec(),
-                    )
-                ]
-            )
-        # otherwise, set the new presence state & update the last sync time,
-        # but don't update last_active_ts as this isn't an indication that
-        # they've been active (even though it's probably been updated by
-        # set_state above)
-        else:
-            await self._update_states(
-                [prev_state.copy_and_replace(last_user_sync_ts=self.clock.time_msec())]
-            )
+        # Note that this causes last_active_ts to be incremented which is not
+        # what the spec wants.
+        await self.set_state(
+            UserID.from_string(user_id),
+            device_id,
+            state={"presence": presence_state},
+            is_sync=True,
+        )
 
         async def _end() -> None:
             try:
-                self.user_to_num_current_syncs[user_id] -= 1
+                self._user_device_to_num_current_syncs[(user_id, device_id)] -= 1
 
                 prev_state = await self.current_state_for_user(user_id)
                 await self._update_states(
@@ -1056,12 +1085,19 @@ class PresenceHandler(BasePresenceHandler):
 
         return _user_syncing()
 
-    def get_currently_syncing_users_for_replication(self) -> Iterable[str]:
+    def get_currently_syncing_users_for_replication(
+        self,
+    ) -> Iterable[Tuple[str, Optional[str]]]:
         # since we are the process handling presence, there is nothing to do here.
         return []
 
     async def update_external_syncs_row(
-        self, process_id: str, user_id: str, is_syncing: bool, sync_time_msec: int
+        self,
+        process_id: str,
+        user_id: str,
+        device_id: Optional[str],
+        is_syncing: bool,
+        sync_time_msec: int,
     ) -> None:
         """Update the syncing users for an external process as a delta.
 
@@ -1070,6 +1106,7 @@ class PresenceHandler(BasePresenceHandler):
                 syncing against. This allows synapse to process updates
                 as user start and stop syncing against a given process.
             user_id: The user who has started or stopped syncing
+            device_id: The user's device that has started or stopped syncing
             is_syncing: Whether or not the user is now syncing
             sync_time_msec: Time in ms when the user was last syncing
         """
@@ -1080,31 +1117,27 @@ class PresenceHandler(BasePresenceHandler):
                 process_id, set()
             )
 
-            updates = []
-            if is_syncing and user_id not in process_presence:
-                if prev_state.state == PresenceState.OFFLINE:
-                    updates.append(
-                        prev_state.copy_and_replace(
-                            state=PresenceState.ONLINE,
-                            last_active_ts=sync_time_msec,
-                            last_user_sync_ts=sync_time_msec,
-                        )
-                    )
-                else:
-                    updates.append(
-                        prev_state.copy_and_replace(last_user_sync_ts=sync_time_msec)
-                    )
-                process_presence.add(user_id)
-            elif user_id in process_presence:
-                updates.append(
-                    prev_state.copy_and_replace(last_user_sync_ts=sync_time_msec)
+            # USER_SYNC is sent when a user's device starts or stops syncing on
+            # a remote # process. (But only for the initial and last sync for that
+            # device.)
+            #
+            # When a device *starts* syncing it also calls set_state(...) which
+            # will update the state, last_active_ts, and last_user_sync_ts.
+            # Simply ensure the user & device is tracked as syncing in this case.
+            #
+            # When a device *stops* syncing, update the last_user_sync_ts and mark
+            # them as no longer syncing. Note this doesn't quite match the
+            # monolith behaviour, which updates last_user_sync_ts at the end of
+            # every sync, not just the last in-flight sync.
+            if is_syncing and (user_id, device_id) not in process_presence:
+                process_presence.add((user_id, device_id))
+            elif not is_syncing and (user_id, device_id) in process_presence:
+                new_state = prev_state.copy_and_replace(
+                    last_user_sync_ts=sync_time_msec
                 )
+                await self._update_states([new_state])
 
-            if not is_syncing:
-                process_presence.discard(user_id)
-
-            if updates:
-                await self._update_states(updates)
+                process_presence.discard((user_id, device_id))
 
             self.external_process_last_updated_ms[process_id] = self.clock.time_msec()
 
@@ -1118,7 +1151,9 @@ class PresenceHandler(BasePresenceHandler):
             process_presence = self.external_process_to_current_syncs.pop(
                 process_id, set()
             )
-            prev_states = await self.current_state_for_users(process_presence)
+            prev_states = await self.current_state_for_users(
+                {user_id for user_id, device_id in process_presence}
+            )
             time_now_ms = self.clock.time_msec()
 
             await self._update_states(
@@ -1203,18 +1238,22 @@ class PresenceHandler(BasePresenceHandler):
     async def set_state(
         self,
         target_user: UserID,
+        device_id: Optional[str],
         state: JsonDict,
-        ignore_status_msg: bool = False,
         force_notify: bool = False,
+        is_sync: bool = False,
     ) -> None:
         """Set the presence state of the user.
 
         Args:
             target_user: The ID of the user to set the presence state of.
+            device_id: the device that the user is setting the presence state of.
             state: The presence state as a JSON dictionary.
-            ignore_status_msg: True to ignore the "status_msg" field of the `state` dict.
-                If False, the user's current status will be updated.
             force_notify: Whether to force notification of the update to clients.
+            is_sync: True if this update was from a sync, which results in
+                *not* overriding a previously set BUSY status, updating the
+                user's last_user_sync_ts, and ignoring the "status_msg" field of
+                the `state` dict.
         """
         status_msg = state.get("status_msg", None)
         presence = state["presence"]
@@ -1227,18 +1266,27 @@ class PresenceHandler(BasePresenceHandler):
             return
 
         user_id = target_user.to_string()
+        now = self.clock.time_msec()
 
         prev_state = await self.current_state_for_user(user_id)
 
+        # Syncs do not override a previous presence of busy.
+        #
+        # TODO: This is a hack for lack of multi-device support. Unfortunately
+        # removing this requires coordination with clients.
+        if prev_state.state == PresenceState.BUSY and is_sync:
+            presence = PresenceState.BUSY
+
         new_fields = {"state": presence}
 
-        if not ignore_status_msg:
-            new_fields["status_msg"] = status_msg
+        if presence == PresenceState.ONLINE or presence == PresenceState.BUSY:
+            new_fields["last_active_ts"] = now
 
-        if presence == PresenceState.ONLINE or (
-            presence == PresenceState.BUSY and self._busy_presence_enabled
-        ):
-            new_fields["last_active_ts"] = self.clock.time_msec()
+        if is_sync:
+            new_fields["last_user_sync_ts"] = now
+        else:
+            # Syncs do not override the status message.
+            new_fields["status_msg"] = status_msg
 
         await self._update_states(
             [prev_state.copy_and_replace(**new_fields)], force_notify=force_notify
@@ -1462,7 +1510,7 @@ class PresenceHandler(BasePresenceHandler):
                 or state.status_msg is not None
             ]
 
-            self._federation_queue.send_presence_to_destinations(
+            await self._federation_queue.send_presence_to_destinations(
                 destinations=newly_joined_remote_hosts,
                 states=states,
             )
@@ -1473,7 +1521,7 @@ class PresenceHandler(BasePresenceHandler):
             prev_remote_hosts or newly_joined_remote_hosts
         ):
             local_states = await self.current_state_for_users(newly_joined_local_users)
-            self._federation_queue.send_presence_to_destinations(
+            await self._federation_queue.send_presence_to_destinations(
                 destinations=prev_remote_hosts | newly_joined_remote_hosts,
                 states=list(local_states.values()),
             )
@@ -2136,7 +2184,7 @@ class PresenceFederationQueue:
         index = bisect(self._queue, (clear_before,))
         self._queue = self._queue[index:]
 
-    def send_presence_to_destinations(
+    async def send_presence_to_destinations(
         self, states: Collection[UserPresenceState], destinations: StrCollection
     ) -> None:
         """Send the presence states to the given destinations.
@@ -2156,7 +2204,7 @@ class PresenceFederationQueue:
             return
 
         if self._federation:
-            self._federation.send_presence_to_destinations(
+            await self._federation.send_presence_to_destinations(
                 states=states,
                 destinations=destinations,
             )
@@ -2279,7 +2327,7 @@ class PresenceFederationQueue:
 
         for host, user_ids in hosts_to_users.items():
             states = await self._presence_handler.current_state_for_users(user_ids)
-            self._federation.send_presence_to_destinations(
+            await self._federation.send_presence_to_destinations(
                 states=states.values(),
                 destinations=[host],
             )
diff --git a/synapse/handlers/room_member.py b/synapse/handlers/room_member.py
index bb409f97b7..da146b0d45 100644
--- a/synapse/handlers/room_member.py
+++ b/synapse/handlers/room_member.py
@@ -112,8 +112,7 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
         self._join_rate_limiter_local = Ratelimiter(
             store=self.store,
             clock=self.clock,
-            rate_hz=hs.config.ratelimiting.rc_joins_local.per_second,
-            burst_count=hs.config.ratelimiting.rc_joins_local.burst_count,
+            cfg=hs.config.ratelimiting.rc_joins_local,
         )
         # Tracks joins from local users to rooms this server isn't a member of.
         # I.e. joins this server makes by requesting /make_join /send_join from
@@ -121,8 +120,7 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
         self._join_rate_limiter_remote = Ratelimiter(
             store=self.store,
             clock=self.clock,
-            rate_hz=hs.config.ratelimiting.rc_joins_remote.per_second,
-            burst_count=hs.config.ratelimiting.rc_joins_remote.burst_count,
+            cfg=hs.config.ratelimiting.rc_joins_remote,
         )
         # TODO: find a better place to keep this Ratelimiter.
         #   It needs to be
@@ -135,8 +133,7 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
         self._join_rate_per_room_limiter = Ratelimiter(
             store=self.store,
             clock=self.clock,
-            rate_hz=hs.config.ratelimiting.rc_joins_per_room.per_second,
-            burst_count=hs.config.ratelimiting.rc_joins_per_room.burst_count,
+            cfg=hs.config.ratelimiting.rc_joins_per_room,
         )
 
         # Ratelimiter for invites, keyed by room (across all issuers, all
@@ -144,8 +141,7 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
         self._invites_per_room_limiter = Ratelimiter(
             store=self.store,
             clock=self.clock,
-            rate_hz=hs.config.ratelimiting.rc_invites_per_room.per_second,
-            burst_count=hs.config.ratelimiting.rc_invites_per_room.burst_count,
+            cfg=hs.config.ratelimiting.rc_invites_per_room,
         )
 
         # Ratelimiter for invites, keyed by recipient (across all rooms, all
@@ -153,8 +149,7 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
         self._invites_per_recipient_limiter = Ratelimiter(
             store=self.store,
             clock=self.clock,
-            rate_hz=hs.config.ratelimiting.rc_invites_per_user.per_second,
-            burst_count=hs.config.ratelimiting.rc_invites_per_user.burst_count,
+            cfg=hs.config.ratelimiting.rc_invites_per_user,
         )
 
         # Ratelimiter for invites, keyed by issuer (across all rooms, all
@@ -162,15 +157,13 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
         self._invites_per_issuer_limiter = Ratelimiter(
             store=self.store,
             clock=self.clock,
-            rate_hz=hs.config.ratelimiting.rc_invites_per_issuer.per_second,
-            burst_count=hs.config.ratelimiting.rc_invites_per_issuer.burst_count,
+            cfg=hs.config.ratelimiting.rc_invites_per_issuer,
         )
 
         self._third_party_invite_limiter = Ratelimiter(
             store=self.store,
             clock=self.clock,
-            rate_hz=hs.config.ratelimiting.rc_third_party_invite.per_second,
-            burst_count=hs.config.ratelimiting.rc_third_party_invite.burst_count,
+            cfg=hs.config.ratelimiting.rc_third_party_invite,
         )
 
         self.request_ratelimiter = hs.get_request_ratelimiter()
diff --git a/synapse/handlers/room_summary.py b/synapse/handlers/room_summary.py
index dad3e23470..dd559b4c45 100644
--- a/synapse/handlers/room_summary.py
+++ b/synapse/handlers/room_summary.py
@@ -35,6 +35,7 @@ from synapse.api.errors import (
     UnsupportedRoomVersionError,
 )
 from synapse.api.ratelimiting import Ratelimiter
+from synapse.config.ratelimiting import RatelimitSettings
 from synapse.events import EventBase
 from synapse.types import JsonDict, Requester, StrCollection
 from synapse.util.caches.response_cache import ResponseCache
@@ -94,7 +95,9 @@ class RoomSummaryHandler:
         self._server_name = hs.hostname
         self._federation_client = hs.get_federation_client()
         self._ratelimiter = Ratelimiter(
-            store=self._store, clock=hs.get_clock(), rate_hz=5, burst_count=10
+            store=self._store,
+            clock=hs.get_clock(),
+            cfg=RatelimitSettings("<room summary>", per_second=5, burst_count=10),
         )
 
         # If a user tries to fetch the same page multiple times in quick succession,
diff --git a/synapse/handlers/send_email.py b/synapse/handlers/send_email.py
index 804cc6e81e..05e21509de 100644
--- a/synapse/handlers/send_email.py
+++ b/synapse/handlers/send_email.py
@@ -23,9 +23,11 @@ from pkg_resources import parse_version
 
 import twisted
 from twisted.internet.defer import Deferred
-from twisted.internet.interfaces import IOpenSSLContextFactory
+from twisted.internet.endpoints import HostnameEndpoint
+from twisted.internet.interfaces import IOpenSSLContextFactory, IProtocolFactory
 from twisted.internet.ssl import optionsForClientTLS
 from twisted.mail.smtp import ESMTPSender, ESMTPSenderFactory
+from twisted.protocols.tls import TLSMemoryBIOFactory
 
 from synapse.logging.context import make_deferred_yieldable
 from synapse.types import ISynapseReactor
@@ -97,6 +99,7 @@ async def _sendmail(
             **kwargs,
         )
 
+    factory: IProtocolFactory
     if _is_old_twisted:
         # before twisted 21.2, we have to override the ESMTPSender protocol to disable
         # TLS
@@ -110,22 +113,13 @@ async def _sendmail(
         factory = build_sender_factory(hostname=smtphost if enable_tls else None)
 
     if force_tls:
-        reactor.connectSSL(
-            smtphost,
-            smtpport,
-            factory,
-            optionsForClientTLS(smtphost),
-            timeout=30,
-            bindAddress=None,
-        )
-    else:
-        reactor.connectTCP(
-            smtphost,
-            smtpport,
-            factory,
-            timeout=30,
-            bindAddress=None,
-        )
+        factory = TLSMemoryBIOFactory(optionsForClientTLS(smtphost), True, factory)
+
+    endpoint = HostnameEndpoint(
+        reactor, smtphost, smtpport, timeout=30, bindAddress=None
+    )
+
+    await make_deferred_yieldable(endpoint.connect(factory))
 
     await make_deferred_yieldable(d)
 
diff --git a/synapse/handlers/typing.py b/synapse/handlers/typing.py
index 7aeae5319c..4b4227003d 100644
--- a/synapse/handlers/typing.py
+++ b/synapse/handlers/typing.py
@@ -26,9 +26,10 @@ from synapse.metrics.background_process_metrics import (
 )
 from synapse.replication.tcp.streams import TypingStream
 from synapse.streams import EventSource
-from synapse.types import JsonDict, Requester, StreamKeyType, UserID
+from synapse.types import JsonDict, Requester, StrCollection, StreamKeyType, UserID
 from synapse.util.caches.stream_change_cache import StreamChangeCache
 from synapse.util.metrics import Measure
+from synapse.util.retryutils import filter_destinations_by_retry_limiter
 from synapse.util.wheel_timer import WheelTimer
 
 if TYPE_CHECKING:
@@ -150,8 +151,15 @@ class FollowerTypingHandler:
                 now=now, obj=member, then=now + FEDERATION_PING_INTERVAL
             )
 
-            hosts = await self._storage_controllers.state.get_current_hosts_in_room(
-                member.room_id
+            hosts: StrCollection = (
+                await self._storage_controllers.state.get_current_hosts_in_room(
+                    member.room_id
+                )
+            )
+            hosts = await filter_destinations_by_retry_limiter(
+                hosts,
+                clock=self.clock,
+                store=self.store,
             )
             for domain in hosts:
                 if not self.is_mine_server_name(domain):
diff --git a/synapse/http/matrixfederationclient.py b/synapse/http/matrixfederationclient.py
index 583c03447c..08c7fc1631 100644
--- a/synapse/http/matrixfederationclient.py
+++ b/synapse/http/matrixfederationclient.py
@@ -243,7 +243,7 @@ class LegacyJsonSendParser(_BaseJsonParser[Tuple[int, JsonDict]]):
         return (
             isinstance(v, list)
             and len(v) == 2
-            and type(v[0]) == int
+            and type(v[0]) == int  # noqa: E721
             and isinstance(v[1], dict)
         )
 
@@ -512,6 +512,7 @@ class MatrixFederationHttpClient:
         long_retries: bool = False,
         ignore_backoff: bool = False,
         backoff_on_404: bool = False,
+        backoff_on_all_error_codes: bool = False,
     ) -> IResponse:
         """
         Sends a request to the given server.
@@ -552,6 +553,7 @@ class MatrixFederationHttpClient:
                 and try the request anyway.
 
             backoff_on_404: Back off if we get a 404
+            backoff_on_all_error_codes: Back off if we get any error response
 
         Returns:
             Resolves with the HTTP response object on success.
@@ -594,6 +596,7 @@ class MatrixFederationHttpClient:
             ignore_backoff=ignore_backoff,
             notifier=self.hs.get_notifier(),
             replication_client=self.hs.get_replication_command_handler(),
+            backoff_on_all_error_codes=backoff_on_all_error_codes,
         )
 
         method_bytes = request.method.encode("ascii")
@@ -889,6 +892,7 @@ class MatrixFederationHttpClient:
         backoff_on_404: bool = False,
         try_trailing_slash_on_400: bool = False,
         parser: Literal[None] = None,
+        backoff_on_all_error_codes: bool = False,
     ) -> JsonDict:
         ...
 
@@ -906,6 +910,7 @@ class MatrixFederationHttpClient:
         backoff_on_404: bool = False,
         try_trailing_slash_on_400: bool = False,
         parser: Optional[ByteParser[T]] = None,
+        backoff_on_all_error_codes: bool = False,
     ) -> T:
         ...
 
@@ -922,6 +927,7 @@ class MatrixFederationHttpClient:
         backoff_on_404: bool = False,
         try_trailing_slash_on_400: bool = False,
         parser: Optional[ByteParser[T]] = None,
+        backoff_on_all_error_codes: bool = False,
     ) -> Union[JsonDict, T]:
         """Sends the specified json data using PUT
 
@@ -957,6 +963,7 @@ class MatrixFederationHttpClient:
                 enabled.
             parser: The parser to use to decode the response. Defaults to
                 parsing as JSON.
+            backoff_on_all_error_codes: Back off if we get any error response
 
         Returns:
             Succeeds when we get a 2xx HTTP response. The
@@ -990,6 +997,7 @@ class MatrixFederationHttpClient:
             ignore_backoff=ignore_backoff,
             long_retries=long_retries,
             timeout=timeout,
+            backoff_on_all_error_codes=backoff_on_all_error_codes,
         )
 
         if timeout is not None:
diff --git a/synapse/http/server.py b/synapse/http/server.py
index 5109cec983..3bbf91298e 100644
--- a/synapse/http/server.py
+++ b/synapse/http/server.py
@@ -115,7 +115,13 @@ def return_json_error(
         if exc.headers is not None:
             for header, value in exc.headers.items():
                 request.setHeader(header, value)
-        logger.info("%s SynapseError: %s - %s", request, error_code, exc.msg)
+        error_ctx = exc.debug_context
+        if error_ctx:
+            logger.info(
+                "%s SynapseError: %s - %s (%s)", request, error_code, exc.msg, error_ctx
+            )
+        else:
+            logger.info("%s SynapseError: %s - %s", request, error_code, exc.msg)
     elif f.check(CancelledError):
         error_code = HTTP_STATUS_REQUEST_CANCELLED
         error_dict = {"error": "Request cancelled", "errcode": Codes.UNKNOWN}
diff --git a/synapse/logging/_terse_json.py b/synapse/logging/_terse_json.py
index b78d6e17c9..98c6038ff2 100644
--- a/synapse/logging/_terse_json.py
+++ b/synapse/logging/_terse_json.py
@@ -44,6 +44,7 @@ _IGNORED_LOG_RECORD_ATTRIBUTES = {
     "processName",
     "relativeCreated",
     "stack_info",
+    "taskName",
     "thread",
     "threadName",
 }
diff --git a/synapse/logging/context.py b/synapse/logging/context.py
index f62bea968f..64c6ae4512 100644
--- a/synapse/logging/context.py
+++ b/synapse/logging/context.py
@@ -809,23 +809,24 @@ def run_in_background(  # type: ignore[misc]
 
     # `res` may be a coroutine, `Deferred`, some other kind of awaitable, or a plain
     # value. Convert it to a `Deferred`.
+    d: "defer.Deferred[R]"
     if isinstance(res, typing.Coroutine):
         # Wrap the coroutine in a `Deferred`.
-        res = defer.ensureDeferred(res)
+        d = defer.ensureDeferred(res)
     elif isinstance(res, defer.Deferred):
-        pass
+        d = res
     elif isinstance(res, Awaitable):
         # `res` is probably some kind of completed awaitable, such as a `DoneAwaitable`
         # or `Future` from `make_awaitable`.
-        res = defer.ensureDeferred(_unwrap_awaitable(res))
+        d = defer.ensureDeferred(_unwrap_awaitable(res))
     else:
         # `res` is a plain value. Wrap it in a `Deferred`.
-        res = defer.succeed(res)
+        d = defer.succeed(res)
 
-    if res.called and not res.paused:
+    if d.called and not d.paused:
         # The function should have maintained the logcontext, so we can
         # optimise out the messing about
-        return res
+        return d
 
     # The function may have reset the context before returning, so
     # we need to restore it now.
@@ -843,8 +844,8 @@ def run_in_background(  # type: ignore[misc]
     # which is supposed to have a single entry and exit point. But
     # by spawning off another deferred, we are effectively
     # adding a new exit point.)
-    res.addBoth(_set_context_cb, ctx)
-    return res
+    d.addBoth(_set_context_cb, ctx)
+    return d
 
 
 T = TypeVar("T")
@@ -877,7 +878,7 @@ def make_deferred_yieldable(deferred: "defer.Deferred[T]") -> "defer.Deferred[T]
 ResultT = TypeVar("ResultT")
 
 
-def _set_context_cb(result: ResultT, context: LoggingContext) -> ResultT:
+def _set_context_cb(result: ResultT, context: LoggingContextOrSentinel) -> ResultT:
     """A callback function which just sets the logging context"""
     set_current_context(context)
     return result
diff --git a/synapse/logging/opentracing.py b/synapse/logging/opentracing.py
index be910128aa..5c3045e197 100644
--- a/synapse/logging/opentracing.py
+++ b/synapse/logging/opentracing.py
@@ -910,10 +910,10 @@ def _custom_sync_async_decorator(
         async def _wrapper(
             *args: P.args, **kwargs: P.kwargs
         ) -> Any:  # Return type is RInner
-            with wrapping_logic(func, *args, **kwargs):
-                # type-ignore: func() returns R, but mypy doesn't know that R is
-                # Awaitable here.
-                return await func(*args, **kwargs)  # type: ignore[misc]
+            # type-ignore: func() returns R, but mypy doesn't know that R is
+            # Awaitable here.
+            with wrapping_logic(func, *args, **kwargs):  # type: ignore[arg-type]
+                return await func(*args, **kwargs)
 
     else:
         # The other case here handles sync functions including those decorated with
@@ -980,8 +980,7 @@ def trace_with_opname(
     See the module's doc string for usage examples.
     """
 
-    # type-ignore: mypy bug, see https://github.com/python/mypy/issues/12909
-    @contextlib.contextmanager  # type: ignore[arg-type]
+    @contextlib.contextmanager
     def _wrapping_logic(
         func: Callable[P, R], *args: P.args, **kwargs: P.kwargs
     ) -> Generator[None, None, None]:
@@ -1024,8 +1023,7 @@ def tag_args(func: Callable[P, R]) -> Callable[P, R]:
     if not opentracing:
         return func
 
-    # type-ignore: mypy bug, see https://github.com/python/mypy/issues/12909
-    @contextlib.contextmanager  # type: ignore[arg-type]
+    @contextlib.contextmanager
     def _wrapping_logic(
         func: Callable[P, R], *args: P.args, **kwargs: P.kwargs
     ) -> Generator[None, None, None]:
diff --git a/synapse/media/media_repository.py b/synapse/media/media_repository.py
index 4b750c700b..1b7b014f9a 100644
--- a/synapse/media/media_repository.py
+++ b/synapse/media/media_repository.py
@@ -214,7 +214,10 @@ class MediaRepository:
             user_id=auth_user,
         )
 
-        await self._generate_thumbnails(None, media_id, media_id, media_type)
+        try:
+            await self._generate_thumbnails(None, media_id, media_id, media_type)
+        except Exception as e:
+            logger.info("Failed to generate thumbnails: %s", e)
 
         return MXCUri(self.server_name, media_id)
 
diff --git a/synapse/media/oembed.py b/synapse/media/oembed.py
index 5ad9eec80b..2ce842c98d 100644
--- a/synapse/media/oembed.py
+++ b/synapse/media/oembed.py
@@ -204,7 +204,7 @@ class OEmbedProvider:
                 calc_description_and_urls(open_graph_response, oembed["html"])
             for size in ("width", "height"):
                 val = oembed.get(size)
-                if type(val) is int:
+                if type(val) is int:  # noqa: E721
                     open_graph_response[f"og:video:{size}"] = val
 
         elif oembed_type == "link":
diff --git a/synapse/media/thumbnailer.py b/synapse/media/thumbnailer.py
index 2bfa58ceee..d8979813b3 100644
--- a/synapse/media/thumbnailer.py
+++ b/synapse/media/thumbnailer.py
@@ -78,7 +78,7 @@ class Thumbnailer:
             image_exif = self.image._getexif()  # type: ignore
             if image_exif is not None:
                 image_orientation = image_exif.get(EXIF_ORIENTATION_TAG)
-                assert type(image_orientation) is int
+                assert type(image_orientation) is int  # noqa: E721
                 self.transpose_method = EXIF_TRANSPOSE_MAPPINGS.get(image_orientation)
         except Exception as e:
             # A lot of parsing errors can happen when parsing EXIF
diff --git a/synapse/module_api/__init__.py b/synapse/module_api/__init__.py
index 9ad8e038ae..2f00a7ba20 100644
--- a/synapse/module_api/__init__.py
+++ b/synapse/module_api/__init__.py
@@ -1180,7 +1180,7 @@ class ModuleApi:
 
             # Send to remote destinations.
             destination = UserID.from_string(user).domain
-            presence_handler.get_federation_queue().send_presence_to_destinations(
+            await presence_handler.get_federation_queue().send_presence_to_destinations(
                 presence_events, [destination]
             )
 
diff --git a/synapse/push/bulk_push_rule_evaluator.py b/synapse/push/bulk_push_rule_evaluator.py
index 990c079c81..554634579e 100644
--- a/synapse/push/bulk_push_rule_evaluator.py
+++ b/synapse/push/bulk_push_rule_evaluator.py
@@ -379,7 +379,7 @@ class BulkPushRuleEvaluator:
             keys = list(notification_levels.keys())
             for key in keys:
                 level = notification_levels.get(key, SENTINEL)
-                if level is not SENTINEL and type(level) is not int:
+                if level is not SENTINEL and type(level) is not int:  # noqa: E721
                     try:
                         notification_levels[key] = int(level)
                     except (TypeError, ValueError):
@@ -472,7 +472,11 @@ StateGroup = Union[object, int]
 
 
 def _is_simple_value(value: Any) -> bool:
-    return isinstance(value, (bool, str)) or type(value) is int or value is None
+    return (
+        isinstance(value, (bool, str))
+        or type(value) is int  # noqa: E721
+        or value is None
+    )
 
 
 def _flatten_dict(
diff --git a/synapse/replication/http/devices.py b/synapse/replication/http/devices.py
index 73f3de3642..209833d287 100644
--- a/synapse/replication/http/devices.py
+++ b/synapse/replication/http/devices.py
@@ -62,7 +62,7 @@ class ReplicationMultiUserDevicesResyncRestServlet(ReplicationEndpoint):
 
     NAME = "multi_user_device_resync"
     PATH_ARGS = ()
-    CACHE = False
+    CACHE = True
 
     def __init__(self, hs: "HomeServer"):
         super().__init__(hs)
diff --git a/synapse/replication/http/presence.py b/synapse/replication/http/presence.py
index db16aac9c2..6c9e79fb07 100644
--- a/synapse/replication/http/presence.py
+++ b/synapse/replication/http/presence.py
@@ -13,7 +13,7 @@
 # limitations under the License.
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING, Optional, Tuple
 
 from twisted.web.server import Request
 
@@ -51,14 +51,14 @@ class ReplicationBumpPresenceActiveTime(ReplicationEndpoint):
         self._presence_handler = hs.get_presence_handler()
 
     @staticmethod
-    async def _serialize_payload(user_id: str) -> JsonDict:  # type: ignore[override]
-        return {}
+    async def _serialize_payload(user_id: str, device_id: Optional[str]) -> JsonDict:  # type: ignore[override]
+        return {"device_id": device_id}
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, user_id: str
     ) -> Tuple[int, JsonDict]:
         await self._presence_handler.bump_presence_active_time(
-            UserID.from_string(user_id)
+            UserID.from_string(user_id), content.get("device_id")
         )
 
         return (200, {})
@@ -73,8 +73,8 @@ class ReplicationPresenceSetState(ReplicationEndpoint):
 
         {
             "state": { ... },
-            "ignore_status_msg": false,
-            "force_notify": false
+            "force_notify": false,
+            "is_sync": false
         }
 
         200 OK
@@ -95,14 +95,16 @@ class ReplicationPresenceSetState(ReplicationEndpoint):
     @staticmethod
     async def _serialize_payload(  # type: ignore[override]
         user_id: str,
+        device_id: Optional[str],
         state: JsonDict,
-        ignore_status_msg: bool = False,
         force_notify: bool = False,
+        is_sync: bool = False,
     ) -> JsonDict:
         return {
+            "device_id": device_id,
             "state": state,
-            "ignore_status_msg": ignore_status_msg,
             "force_notify": force_notify,
+            "is_sync": is_sync,
         }
 
     async def _handle_request(  # type: ignore[override]
@@ -110,9 +112,10 @@ class ReplicationPresenceSetState(ReplicationEndpoint):
     ) -> Tuple[int, JsonDict]:
         await self._presence_handler.set_state(
             UserID.from_string(user_id),
+            content.get("device_id"),
             content["state"],
-            content["ignore_status_msg"],
             content["force_notify"],
+            content.get("is_sync", False),
         )
 
         return (200, {})
diff --git a/synapse/replication/tcp/client.py b/synapse/replication/tcp/client.py
index 3b88dc68ea..51285e6d33 100644
--- a/synapse/replication/tcp/client.py
+++ b/synapse/replication/tcp/client.py
@@ -422,7 +422,7 @@ class FederationSenderHandler:
         # The federation stream contains things that we want to send out, e.g.
         # presence, typing, etc.
         if stream_name == "federation":
-            send_queue.process_rows_for_federation(self.federation_sender, rows)
+            await send_queue.process_rows_for_federation(self.federation_sender, rows)
             await self.update_token(token)
 
         # ... and when new receipts happen
@@ -439,16 +439,14 @@ class FederationSenderHandler:
                 for row in rows
                 if not row.entity.startswith("@") and not row.is_signature
             }
-            for host in hosts:
-                self.federation_sender.send_device_messages(host, immediate=False)
+            await self.federation_sender.send_device_messages(hosts, immediate=False)
 
         elif stream_name == ToDeviceStream.NAME:
             # The to_device stream includes stuff to be pushed to both local
             # clients and remote servers, so we ignore entities that start with
             # '@' (since they'll be local users rather than destinations).
             hosts = {row.entity for row in rows if not row.entity.startswith("@")}
-            for host in hosts:
-                self.federation_sender.send_device_messages(host)
+            await self.federation_sender.send_device_messages(hosts)
 
     async def _on_new_receipts(
         self, rows: Iterable[ReceiptsStream.ReceiptsStreamRow]
diff --git a/synapse/replication/tcp/commands.py b/synapse/replication/tcp/commands.py
index 10f5c98ff8..e616b5e1c8 100644
--- a/synapse/replication/tcp/commands.py
+++ b/synapse/replication/tcp/commands.py
@@ -267,27 +267,38 @@ class UserSyncCommand(Command):
     NAME = "USER_SYNC"
 
     def __init__(
-        self, instance_id: str, user_id: str, is_syncing: bool, last_sync_ms: int
+        self,
+        instance_id: str,
+        user_id: str,
+        device_id: Optional[str],
+        is_syncing: bool,
+        last_sync_ms: int,
     ):
         self.instance_id = instance_id
         self.user_id = user_id
+        self.device_id = device_id
         self.is_syncing = is_syncing
         self.last_sync_ms = last_sync_ms
 
     @classmethod
     def from_line(cls: Type["UserSyncCommand"], line: str) -> "UserSyncCommand":
-        instance_id, user_id, state, last_sync_ms = line.split(" ", 3)
+        device_id: Optional[str]
+        instance_id, user_id, device_id, state, last_sync_ms = line.split(" ", 4)
+
+        if device_id == "None":
+            device_id = None
 
         if state not in ("start", "end"):
             raise Exception("Invalid USER_SYNC state %r" % (state,))
 
-        return cls(instance_id, user_id, state == "start", int(last_sync_ms))
+        return cls(instance_id, user_id, device_id, state == "start", int(last_sync_ms))
 
     def to_line(self) -> str:
         return " ".join(
             (
                 self.instance_id,
                 self.user_id,
+                str(self.device_id),
                 "start" if self.is_syncing else "end",
                 str(self.last_sync_ms),
             )
@@ -452,6 +463,17 @@ class LockReleasedCommand(Command):
         return json_encoder.encode([self.instance_name, self.lock_name, self.lock_key])
 
 
+class NewActiveTaskCommand(_SimpleCommand):
+    """Sent to inform instance handling background tasks that a new active task is available to run.
+
+    Format::
+
+        NEW_ACTIVE_TASK "<task_id>"
+    """
+
+    NAME = "NEW_ACTIVE_TASK"
+
+
 _COMMANDS: Tuple[Type[Command], ...] = (
     ServerCommand,
     RdataCommand,
@@ -466,6 +488,7 @@ _COMMANDS: Tuple[Type[Command], ...] = (
     RemoteServerUpCommand,
     ClearUserSyncsCommand,
     LockReleasedCommand,
+    NewActiveTaskCommand,
 )
 
 # Map of command name to command type.
diff --git a/synapse/replication/tcp/handler.py b/synapse/replication/tcp/handler.py
index 38adcbe1d0..d9045d7b73 100644
--- a/synapse/replication/tcp/handler.py
+++ b/synapse/replication/tcp/handler.py
@@ -40,6 +40,7 @@ from synapse.replication.tcp.commands import (
     Command,
     FederationAckCommand,
     LockReleasedCommand,
+    NewActiveTaskCommand,
     PositionCommand,
     RdataCommand,
     RemoteServerUpCommand,
@@ -238,6 +239,10 @@ class ReplicationCommandHandler:
         if self._is_master:
             self._server_notices_sender = hs.get_server_notices_sender()
 
+        self._task_scheduler = None
+        if hs.config.worker.run_background_tasks:
+            self._task_scheduler = hs.get_task_scheduler()
+
         if hs.config.redis.redis_enabled:
             # If we're using Redis, it's the background worker that should
             # receive USER_IP commands and store the relevant client IPs.
@@ -423,7 +428,11 @@ class ReplicationCommandHandler:
 
         if self._is_presence_writer:
             return self._presence_handler.update_external_syncs_row(
-                cmd.instance_id, cmd.user_id, cmd.is_syncing, cmd.last_sync_ms
+                cmd.instance_id,
+                cmd.user_id,
+                cmd.device_id,
+                cmd.is_syncing,
+                cmd.last_sync_ms,
             )
         else:
             return None
@@ -663,6 +672,15 @@ class ReplicationCommandHandler:
             cmd.instance_name, cmd.lock_name, cmd.lock_key
         )
 
+    async def on_NEW_ACTIVE_TASK(
+        self, conn: IReplicationConnection, cmd: NewActiveTaskCommand
+    ) -> None:
+        """Called when get a new NEW_ACTIVE_TASK command."""
+        if self._task_scheduler:
+            task = await self._task_scheduler.get_task(cmd.data)
+            if task:
+                await self._task_scheduler._launch_task(task)
+
     def new_connection(self, connection: IReplicationConnection) -> None:
         """Called when we have a new connection."""
         self._connections.append(connection)
@@ -685,9 +703,9 @@ class ReplicationCommandHandler:
         )
 
         now = self._clock.time_msec()
-        for user_id in currently_syncing:
+        for user_id, device_id in currently_syncing:
             connection.send_command(
-                UserSyncCommand(self._instance_id, user_id, True, now)
+                UserSyncCommand(self._instance_id, user_id, device_id, True, now)
             )
 
     def lost_connection(self, connection: IReplicationConnection) -> None:
@@ -739,11 +757,16 @@ class ReplicationCommandHandler:
         self.send_command(FederationAckCommand(self._instance_name, token))
 
     def send_user_sync(
-        self, instance_id: str, user_id: str, is_syncing: bool, last_sync_ms: int
+        self,
+        instance_id: str,
+        user_id: str,
+        device_id: Optional[str],
+        is_syncing: bool,
+        last_sync_ms: int,
     ) -> None:
         """Poke the master that a user has started/stopped syncing."""
         self.send_command(
-            UserSyncCommand(instance_id, user_id, is_syncing, last_sync_ms)
+            UserSyncCommand(instance_id, user_id, device_id, is_syncing, last_sync_ms)
         )
 
     def send_user_ip(
@@ -776,6 +799,10 @@ class ReplicationCommandHandler:
         if instance_name == self._instance_name:
             self.send_command(LockReleasedCommand(instance_name, lock_name, lock_key))
 
+    def send_new_active_task(self, task_id: str) -> None:
+        """Called when a new task has been scheduled for immediate launch and is ACTIVE."""
+        self.send_command(NewActiveTaskCommand(task_id))
+
 
 UpdateToken = TypeVar("UpdateToken")
 UpdateRow = TypeVar("UpdateRow")
diff --git a/synapse/rest/admin/__init__.py b/synapse/rest/admin/__init__.py
index 55e752fda8..94170715fb 100644
--- a/synapse/rest/admin/__init__.py
+++ b/synapse/rest/admin/__init__.py
@@ -157,7 +157,7 @@ class PurgeHistoryRestServlet(RestServlet):
             logger.info("[purge] purging up to token %s (event_id %s)", token, event_id)
         elif "purge_up_to_ts" in body:
             ts = body["purge_up_to_ts"]
-            if type(ts) is not int:
+            if type(ts) is not int:  # noqa: E721
                 raise SynapseError(
                     HTTPStatus.BAD_REQUEST,
                     "purge_up_to_ts must be an int",
diff --git a/synapse/rest/admin/registration_tokens.py b/synapse/rest/admin/registration_tokens.py
index 95e751288b..ffce92d45e 100644
--- a/synapse/rest/admin/registration_tokens.py
+++ b/synapse/rest/admin/registration_tokens.py
@@ -143,7 +143,7 @@ class NewRegistrationTokenRestServlet(RestServlet):
         else:
             # Get length of token to generate (default is 16)
             length = body.get("length", 16)
-            if type(length) is not int:
+            if type(length) is not int:  # noqa: E721
                 raise SynapseError(
                     HTTPStatus.BAD_REQUEST,
                     "length must be an integer",
@@ -163,7 +163,8 @@ class NewRegistrationTokenRestServlet(RestServlet):
 
         uses_allowed = body.get("uses_allowed", None)
         if not (
-            uses_allowed is None or (type(uses_allowed) is int and uses_allowed >= 0)
+            uses_allowed is None
+            or (type(uses_allowed) is int and uses_allowed >= 0)  # noqa: E721
         ):
             raise SynapseError(
                 HTTPStatus.BAD_REQUEST,
@@ -172,13 +173,16 @@ class NewRegistrationTokenRestServlet(RestServlet):
             )
 
         expiry_time = body.get("expiry_time", None)
-        if type(expiry_time) not in (int, type(None)):
+        if expiry_time is not None and type(expiry_time) is not int:  # noqa: E721
             raise SynapseError(
                 HTTPStatus.BAD_REQUEST,
                 "expiry_time must be an integer or null",
                 Codes.INVALID_PARAM,
             )
-        if type(expiry_time) is int and expiry_time < self.clock.time_msec():
+        if (
+            type(expiry_time) is int  # noqa: E721
+            and expiry_time < self.clock.time_msec()
+        ):
             raise SynapseError(
                 HTTPStatus.BAD_REQUEST,
                 "expiry_time must not be in the past",
@@ -283,7 +287,7 @@ class RegistrationTokenRestServlet(RestServlet):
             uses_allowed = body["uses_allowed"]
             if not (
                 uses_allowed is None
-                or (type(uses_allowed) is int and uses_allowed >= 0)
+                or (type(uses_allowed) is int and uses_allowed >= 0)  # noqa: E721
             ):
                 raise SynapseError(
                     HTTPStatus.BAD_REQUEST,
@@ -294,13 +298,16 @@ class RegistrationTokenRestServlet(RestServlet):
 
         if "expiry_time" in body:
             expiry_time = body["expiry_time"]
-            if type(expiry_time) not in (int, type(None)):
+            if expiry_time is not None and type(expiry_time) is not int:  # noqa: E721
                 raise SynapseError(
                     HTTPStatus.BAD_REQUEST,
                     "expiry_time must be an integer or null",
                     Codes.INVALID_PARAM,
                 )
-            if type(expiry_time) is int and expiry_time < self.clock.time_msec():
+            if (
+                type(expiry_time) is int  # noqa: E721
+                and expiry_time < self.clock.time_msec()
+            ):
                 raise SynapseError(
                     HTTPStatus.BAD_REQUEST,
                     "expiry_time must not be in the past",
diff --git a/synapse/rest/admin/users.py b/synapse/rest/admin/users.py
index 240e6254b0..91898a5c13 100644
--- a/synapse/rest/admin/users.py
+++ b/synapse/rest/admin/users.py
@@ -132,6 +132,7 @@ class UsersRestServletV2(RestServlet):
                 UserSortOrder.AVATAR_URL.value,
                 UserSortOrder.SHADOW_BANNED.value,
                 UserSortOrder.CREATION_TS.value,
+                UserSortOrder.LAST_SEEN_TS.value,
             ),
         )
 
@@ -1172,14 +1173,17 @@ class RateLimitRestServlet(RestServlet):
         messages_per_second = body.get("messages_per_second", 0)
         burst_count = body.get("burst_count", 0)
 
-        if type(messages_per_second) is not int or messages_per_second < 0:
+        if (
+            type(messages_per_second) is not int  # noqa: E721
+            or messages_per_second < 0
+        ):
             raise SynapseError(
                 HTTPStatus.BAD_REQUEST,
                 "%r parameter must be a positive int" % (messages_per_second,),
                 errcode=Codes.INVALID_PARAM,
             )
 
-        if type(burst_count) is not int or burst_count < 0:
+        if type(burst_count) is not int or burst_count < 0:  # noqa: E721
             raise SynapseError(
                 HTTPStatus.BAD_REQUEST,
                 "%r parameter must be a positive int" % (burst_count,),
diff --git a/synapse/rest/client/login.py b/synapse/rest/client/login.py
index d724c68920..7be327e26f 100644
--- a/synapse/rest/client/login.py
+++ b/synapse/rest/client/login.py
@@ -120,14 +120,12 @@ class LoginRestServlet(RestServlet):
         self._address_ratelimiter = Ratelimiter(
             store=self._main_store,
             clock=hs.get_clock(),
-            rate_hz=self.hs.config.ratelimiting.rc_login_address.per_second,
-            burst_count=self.hs.config.ratelimiting.rc_login_address.burst_count,
+            cfg=self.hs.config.ratelimiting.rc_login_address,
         )
         self._account_ratelimiter = Ratelimiter(
             store=self._main_store,
             clock=hs.get_clock(),
-            rate_hz=self.hs.config.ratelimiting.rc_login_account.per_second,
-            burst_count=self.hs.config.ratelimiting.rc_login_account.burst_count,
+            cfg=self.hs.config.ratelimiting.rc_login_account,
         )
 
         # ensure the CAS/SAML/OIDC handlers are loaded on this worker instance.
diff --git a/synapse/rest/client/login_token_request.py b/synapse/rest/client/login_token_request.py
index b1629f94a5..d189a923b5 100644
--- a/synapse/rest/client/login_token_request.py
+++ b/synapse/rest/client/login_token_request.py
@@ -16,6 +16,7 @@ import logging
 from typing import TYPE_CHECKING, Tuple
 
 from synapse.api.ratelimiting import Ratelimiter
+from synapse.config.ratelimiting import RatelimitSettings
 from synapse.http.server import HttpServer
 from synapse.http.servlet import RestServlet, parse_json_object_from_request
 from synapse.http.site import SynapseRequest
@@ -66,15 +67,18 @@ class LoginTokenRequestServlet(RestServlet):
         self.token_timeout = hs.config.auth.login_via_existing_token_timeout
         self._require_ui_auth = hs.config.auth.login_via_existing_require_ui_auth
 
-        # Ratelimit aggressively to a maxmimum of 1 request per minute.
+        # Ratelimit aggressively to a maximum of 1 request per minute.
         #
         # This endpoint can be used to spawn additional sessions and could be
         # abused by a malicious client to create many sessions.
         self._ratelimiter = Ratelimiter(
             store=self._main_store,
             clock=hs.get_clock(),
-            rate_hz=1 / 60,
-            burst_count=1,
+            cfg=RatelimitSettings(
+                key="<login token request>",
+                per_second=1 / 60,
+                burst_count=1,
+            ),
         )
 
     @interactive_auth_handler
diff --git a/synapse/rest/client/presence.py b/synapse/rest/client/presence.py
index 8e193330f8..d578faa969 100644
--- a/synapse/rest/client/presence.py
+++ b/synapse/rest/client/presence.py
@@ -97,7 +97,7 @@ class PresenceStatusRestServlet(RestServlet):
             raise SynapseError(400, "Unable to parse state")
 
         if self._use_presence:
-            await self.presence_handler.set_state(user, state)
+            await self.presence_handler.set_state(user, requester.device_id, state)
 
         return 200, {}
 
diff --git a/synapse/rest/client/read_marker.py b/synapse/rest/client/read_marker.py
index 4f96e51eeb..1707e51972 100644
--- a/synapse/rest/client/read_marker.py
+++ b/synapse/rest/client/read_marker.py
@@ -52,7 +52,9 @@ class ReadMarkerRestServlet(RestServlet):
     ) -> Tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
-        await self.presence_handler.bump_presence_active_time(requester.user)
+        await self.presence_handler.bump_presence_active_time(
+            requester.user, requester.device_id
+        )
 
         body = parse_json_object_from_request(request)
 
diff --git a/synapse/rest/client/receipts.py b/synapse/rest/client/receipts.py
index 316e7b9982..869a374459 100644
--- a/synapse/rest/client/receipts.py
+++ b/synapse/rest/client/receipts.py
@@ -94,7 +94,9 @@ class ReceiptRestServlet(RestServlet):
                     Codes.INVALID_PARAM,
                 )
 
-        await self.presence_handler.bump_presence_active_time(requester.user)
+        await self.presence_handler.bump_presence_active_time(
+            requester.user, requester.device_id
+        )
 
         if receipt_type == ReceiptTypes.FULLY_READ:
             await self.read_marker_handler.received_client_read_marker(
diff --git a/synapse/rest/client/register.py b/synapse/rest/client/register.py
index 77e3b91b79..132623462a 100644
--- a/synapse/rest/client/register.py
+++ b/synapse/rest/client/register.py
@@ -376,8 +376,7 @@ class RegistrationTokenValidityRestServlet(RestServlet):
         self.ratelimiter = Ratelimiter(
             store=self.store,
             clock=hs.get_clock(),
-            rate_hz=hs.config.ratelimiting.rc_registration_token_validity.per_second,
-            burst_count=hs.config.ratelimiting.rc_registration_token_validity.burst_count,
+            cfg=hs.config.ratelimiting.rc_registration_token_validity,
         )
 
     async def on_GET(self, request: Request) -> Tuple[int, JsonDict]:
diff --git a/synapse/rest/client/report_event.py b/synapse/rest/client/report_event.py
index ac1a63ca27..ee93e459f6 100644
--- a/synapse/rest/client/report_event.py
+++ b/synapse/rest/client/report_event.py
@@ -55,7 +55,7 @@ class ReportEventRestServlet(RestServlet):
                 "Param 'reason' must be a string",
                 Codes.BAD_JSON,
             )
-        if type(body.get("score", 0)) is not int:
+        if type(body.get("score", 0)) is not int:  # noqa: E721
             raise SynapseError(
                 HTTPStatus.BAD_REQUEST,
                 "Param 'score' must be an integer",
diff --git a/synapse/rest/client/room.py b/synapse/rest/client/room.py
index dc498001e4..553938ce9d 100644
--- a/synapse/rest/client/room.py
+++ b/synapse/rest/client/room.py
@@ -1229,7 +1229,9 @@ class RoomTypingRestServlet(RestServlet):
 
         content = parse_json_object_from_request(request)
 
-        await self.presence_handler.bump_presence_active_time(requester.user)
+        await self.presence_handler.bump_presence_active_time(
+            requester.user, requester.device_id
+        )
 
         # Limit timeout to stop people from setting silly typing timeouts.
         timeout = min(content.get("timeout", 30000), 120000)
diff --git a/synapse/rest/client/sync.py b/synapse/rest/client/sync.py
index d7854ed4fd..42bdd3bb10 100644
--- a/synapse/rest/client/sync.py
+++ b/synapse/rest/client/sync.py
@@ -205,6 +205,7 @@ class SyncRestServlet(RestServlet):
 
         context = await self.presence_handler.user_syncing(
             user.to_string(),
+            requester.device_id,
             affect_presence=affect_presence,
             presence_state=set_presence,
         )
diff --git a/synapse/rest/key/v2/remote_key_resource.py b/synapse/rest/key/v2/remote_key_resource.py
index 981fd1f58a..0aaa838d04 100644
--- a/synapse/rest/key/v2/remote_key_resource.py
+++ b/synapse/rest/key/v2/remote_key_resource.py
@@ -16,6 +16,7 @@ import logging
 import re
 from typing import TYPE_CHECKING, Dict, Mapping, Optional, Set, Tuple
 
+from pydantic import Extra, StrictInt, StrictStr
 from signedjson.sign import sign_json
 
 from twisted.web.server import Request
@@ -24,9 +25,10 @@ from synapse.crypto.keyring import ServerKeyFetcher
 from synapse.http.server import HttpServer
 from synapse.http.servlet import (
     RestServlet,
+    parse_and_validate_json_object_from_request,
     parse_integer,
-    parse_json_object_from_request,
 )
+from synapse.rest.models import RequestBodyModel
 from synapse.storage.keys import FetchKeyResultForRemote
 from synapse.types import JsonDict
 from synapse.util import json_decoder
@@ -38,6 +40,13 @@ if TYPE_CHECKING:
 logger = logging.getLogger(__name__)
 
 
+class _KeyQueryCriteriaDataModel(RequestBodyModel):
+    class Config:
+        extra = Extra.allow
+
+    minimum_valid_until_ts: Optional[StrictInt]
+
+
 class RemoteKey(RestServlet):
     """HTTP resource for retrieving the TLS certificate and NACL signature
     verification keys for a collection of servers. Checks that the reported
@@ -96,6 +105,9 @@ class RemoteKey(RestServlet):
 
     CATEGORY = "Federation requests"
 
+    class PostBody(RequestBodyModel):
+        server_keys: Dict[StrictStr, Dict[StrictStr, _KeyQueryCriteriaDataModel]]
+
     def __init__(self, hs: "HomeServer"):
         self.fetcher = ServerKeyFetcher(hs)
         self.store = hs.get_datastores().main
@@ -137,24 +149,29 @@ class RemoteKey(RestServlet):
             )
 
             minimum_valid_until_ts = parse_integer(request, "minimum_valid_until_ts")
-            arguments = {}
-            if minimum_valid_until_ts is not None:
-                arguments["minimum_valid_until_ts"] = minimum_valid_until_ts
-            query = {server: {key_id: arguments}}
+            query = {
+                server: {
+                    key_id: _KeyQueryCriteriaDataModel(
+                        minimum_valid_until_ts=minimum_valid_until_ts
+                    )
+                }
+            }
         else:
             query = {server: {}}
 
         return 200, await self.query_keys(query, query_remote_on_cache_miss=True)
 
     async def on_POST(self, request: Request) -> Tuple[int, JsonDict]:
-        content = parse_json_object_from_request(request)
+        content = parse_and_validate_json_object_from_request(request, self.PostBody)
 
-        query = content["server_keys"]
+        query = content.server_keys
 
         return 200, await self.query_keys(query, query_remote_on_cache_miss=True)
 
     async def query_keys(
-        self, query: JsonDict, query_remote_on_cache_miss: bool = False
+        self,
+        query: Dict[str, Dict[str, _KeyQueryCriteriaDataModel]],
+        query_remote_on_cache_miss: bool = False,
     ) -> JsonDict:
         logger.info("Handling query for keys %r", query)
 
@@ -196,8 +213,10 @@ class RemoteKey(RestServlet):
             else:
                 ts_added_ms = key_result.added_ts
                 ts_valid_until_ms = key_result.valid_until_ts
-                req_key = query.get(server_name, {}).get(key_id, {})
-                req_valid_until = req_key.get("minimum_valid_until_ts")
+                req_key = query.get(server_name, {}).get(
+                    key_id, _KeyQueryCriteriaDataModel(minimum_valid_until_ts=None)
+                )
+                req_valid_until = req_key.minimum_valid_until_ts
                 if req_valid_until is not None:
                     if ts_valid_until_ms < req_valid_until:
                         logger.debug(
diff --git a/synapse/server.py b/synapse/server.py
index 8f5e4fc140..71ead524d6 100644
--- a/synapse/server.py
+++ b/synapse/server.py
@@ -408,8 +408,7 @@ class HomeServer(metaclass=abc.ABCMeta):
         return Ratelimiter(
             store=self.get_datastores().main,
             clock=self.get_clock(),
-            rate_hz=self.config.ratelimiting.rc_registration.per_second,
-            burst_count=self.config.ratelimiting.rc_registration.burst_count,
+            cfg=self.config.ratelimiting.rc_registration,
         )
 
     @cache_in_self
diff --git a/synapse/storage/background_updates.py b/synapse/storage/background_updates.py
index ddca0af1da..7619f405fa 100644
--- a/synapse/storage/background_updates.py
+++ b/synapse/storage/background_updates.py
@@ -405,14 +405,14 @@ class BackgroundUpdater:
                 try:
                     result = await self.do_next_background_update(sleep)
                     back_to_back_failures = 0
-                except Exception:
+                except Exception as e:
+                    logger.exception("Error doing update: %s", e)
                     back_to_back_failures += 1
                     if back_to_back_failures >= 5:
                         self._aborted = True
                         raise RuntimeError(
                             "5 back-to-back background update failures; aborting."
                         )
-                    logger.exception("Error doing update")
                 else:
                     if result:
                         logger.info(
diff --git a/synapse/storage/database.py b/synapse/storage/database.py
index a1c8fb0f46..55ac313f33 100644
--- a/synapse/storage/database.py
+++ b/synapse/storage/database.py
@@ -31,6 +31,7 @@ from typing import (
     Iterator,
     List,
     Optional,
+    Sequence,
     Tuple,
     Type,
     TypeVar,
@@ -358,7 +359,21 @@ class LoggingTransaction:
         return self.txn.rowcount
 
     @property
-    def description(self) -> Any:
+    def description(
+        self,
+    ) -> Optional[
+        Sequence[
+            Tuple[
+                str,
+                Optional[Any],
+                Optional[int],
+                Optional[int],
+                Optional[int],
+                Optional[int],
+                Optional[int],
+            ]
+        ]
+    ]:
         return self.txn.description
 
     def execute_batch(self, sql: str, args: Iterable[Iterable[Any]]) -> None:
diff --git a/synapse/storage/databases/main/__init__.py b/synapse/storage/databases/main/__init__.py
index a85633efcd..0836e247ef 100644
--- a/synapse/storage/databases/main/__init__.py
+++ b/synapse/storage/databases/main/__init__.py
@@ -277,6 +277,10 @@ class DataStore(
                 FROM users as u
                 LEFT JOIN profiles AS p ON u.name = p.full_user_id
                 LEFT JOIN erased_users AS eu ON u.name = eu.user_id
+                LEFT JOIN (
+                    SELECT user_id, MAX(last_seen) AS last_seen_ts
+                    FROM user_ips GROUP BY user_id
+                ) ls ON u.name = ls.user_id
                 {where_clause}
                 """
             sql = "SELECT COUNT(*) as total_users " + sql_base
@@ -286,7 +290,7 @@ class DataStore(
             sql = f"""
                 SELECT name, user_type, is_guest, admin, deactivated, shadow_banned,
                 displayname, avatar_url, creation_ts * 1000 as creation_ts, approved,
-                eu.user_id is not null as erased
+                eu.user_id is not null as erased, last_seen_ts
                 {sql_base}
                 ORDER BY {order_by_column} {order}, u.name ASC
                 LIMIT ? OFFSET ?
diff --git a/synapse/storage/databases/main/events.py b/synapse/storage/databases/main/events.py
index c1353b18c1..0c1ed75240 100644
--- a/synapse/storage/databases/main/events.py
+++ b/synapse/storage/databases/main/events.py
@@ -978,26 +978,12 @@ class PersistEventsStore:
         """Persist the mapping from transaction IDs to event IDs (if defined)."""
 
         inserted_ts = self._clock.time_msec()
-        to_insert_token_id: List[Tuple[str, str, str, int, str, int]] = []
         to_insert_device_id: List[Tuple[str, str, str, str, str, int]] = []
         for event, _ in events_and_contexts:
             txn_id = getattr(event.internal_metadata, "txn_id", None)
-            token_id = getattr(event.internal_metadata, "token_id", None)
             device_id = getattr(event.internal_metadata, "device_id", None)
 
             if txn_id is not None:
-                if token_id is not None:
-                    to_insert_token_id.append(
-                        (
-                            event.event_id,
-                            event.room_id,
-                            event.sender,
-                            token_id,
-                            txn_id,
-                            inserted_ts,
-                        )
-                    )
-
                 if device_id is not None:
                     to_insert_device_id.append(
                         (
@@ -1010,26 +996,7 @@ class PersistEventsStore:
                         )
                     )
 
-        # Synapse usually relies on the device_id to scope transactions for events,
-        # except for users without device IDs (appservice, guests, and access
-        # tokens minted with the admin API) which use the access token ID instead.
-        #
-        # TODO https://github.com/matrix-org/synapse/issues/16042
-        if to_insert_token_id:
-            self.db_pool.simple_insert_many_txn(
-                txn,
-                table="event_txn_id",
-                keys=(
-                    "event_id",
-                    "room_id",
-                    "user_id",
-                    "token_id",
-                    "txn_id",
-                    "inserted_ts",
-                ),
-                values=to_insert_token_id,
-            )
-
+        # Synapse relies on the device_id to scope transactions for events..
         if to_insert_device_id:
             self.db_pool.simple_insert_many_txn(
                 txn,
@@ -1671,7 +1638,7 @@ class PersistEventsStore:
             if self._ephemeral_messages_enabled:
                 # If there's an expiry timestamp on the event, store it.
                 expiry_ts = event.content.get(EventContentFields.SELF_DESTRUCT_AFTER)
-                if type(expiry_ts) is int and not event.is_state():
+                if type(expiry_ts) is int and not event.is_state():  # noqa: E721
                     self._insert_event_expiry_txn(txn, event.event_id, expiry_ts)
 
         # Insert into the room_memberships table.
@@ -2039,10 +2006,10 @@ class PersistEventsStore:
         ):
             if (
                 "min_lifetime" in event.content
-                and type(event.content["min_lifetime"]) is not int
+                and type(event.content["min_lifetime"]) is not int  # noqa: E721
             ) or (
                 "max_lifetime" in event.content
-                and type(event.content["max_lifetime"]) is not int
+                and type(event.content["max_lifetime"]) is not int  # noqa: E721
             ):
                 # Ignore the event if one of the value isn't an integer.
                 return
diff --git a/synapse/storage/databases/main/events_worker.py b/synapse/storage/databases/main/events_worker.py
index d0dd455aec..943666ed4f 100644
--- a/synapse/storage/databases/main/events_worker.py
+++ b/synapse/storage/databases/main/events_worker.py
@@ -2022,25 +2022,6 @@ class EventsWorkerStore(SQLBaseStore):
             desc="get_next_event_to_expire", func=get_next_event_to_expire_txn
         )
 
-    async def get_event_id_from_transaction_id_and_token_id(
-        self, room_id: str, user_id: str, token_id: int, txn_id: str
-    ) -> Optional[str]:
-        """Look up if we have already persisted an event for the transaction ID,
-        returning the event ID if so.
-        """
-        return await self.db_pool.simple_select_one_onecol(
-            table="event_txn_id",
-            keyvalues={
-                "room_id": room_id,
-                "user_id": user_id,
-                "token_id": token_id,
-                "txn_id": txn_id,
-            },
-            retcol="event_id",
-            allow_none=True,
-            desc="get_event_id_from_transaction_id_and_token_id",
-        )
-
     async def get_event_id_from_transaction_id_and_device_id(
         self, room_id: str, user_id: str, device_id: str, txn_id: str
     ) -> Optional[str]:
@@ -2072,29 +2053,35 @@ class EventsWorkerStore(SQLBaseStore):
         """
 
         mapping = {}
-        txn_id_to_event: Dict[Tuple[str, int, str], str] = {}
+        txn_id_to_event: Dict[Tuple[str, str, str, str], str] = {}
 
         for event in events:
-            token_id = getattr(event.internal_metadata, "token_id", None)
+            device_id = getattr(event.internal_metadata, "device_id", None)
             txn_id = getattr(event.internal_metadata, "txn_id", None)
 
-            if token_id and txn_id:
+            if device_id and txn_id:
                 # Check if this is a duplicate of an event in the given events.
-                existing = txn_id_to_event.get((event.room_id, token_id, txn_id))
+                existing = txn_id_to_event.get(
+                    (event.room_id, event.sender, device_id, txn_id)
+                )
                 if existing:
                     mapping[event.event_id] = existing
                     continue
 
                 # Check if this is a duplicate of an event we've already
                 # persisted.
-                existing = await self.get_event_id_from_transaction_id_and_token_id(
-                    event.room_id, event.sender, token_id, txn_id
+                existing = await self.get_event_id_from_transaction_id_and_device_id(
+                    event.room_id, event.sender, device_id, txn_id
                 )
                 if existing:
                     mapping[event.event_id] = existing
-                    txn_id_to_event[(event.room_id, token_id, txn_id)] = existing
+                    txn_id_to_event[
+                        (event.room_id, event.sender, device_id, txn_id)
+                    ] = existing
                 else:
-                    txn_id_to_event[(event.room_id, token_id, txn_id)] = event.event_id
+                    txn_id_to_event[
+                        (event.room_id, event.sender, device_id, txn_id)
+                    ] = event.event_id
 
         return mapping
 
diff --git a/synapse/storage/databases/main/lock.py b/synapse/storage/databases/main/lock.py
index 54d40e7a3a..5a01ec2137 100644
--- a/synapse/storage/databases/main/lock.py
+++ b/synapse/storage/databases/main/lock.py
@@ -17,7 +17,7 @@ from types import TracebackType
 from typing import TYPE_CHECKING, Collection, Optional, Set, Tuple, Type
 from weakref import WeakValueDictionary
 
-from twisted.internet.interfaces import IReactorCore
+from twisted.internet.task import LoopingCall
 
 from synapse.metrics.background_process_metrics import wrap_as_background_process
 from synapse.storage._base import SQLBaseStore
@@ -26,6 +26,7 @@ from synapse.storage.database import (
     LoggingDatabaseConnection,
     LoggingTransaction,
 )
+from synapse.types import ISynapseReactor
 from synapse.util import Clock
 from synapse.util.stringutils import random_string
 
@@ -358,7 +359,7 @@ class Lock:
 
     def __init__(
         self,
-        reactor: IReactorCore,
+        reactor: ISynapseReactor,
         clock: Clock,
         store: LockStore,
         read_write: bool,
@@ -377,19 +378,25 @@ class Lock:
 
         self._table = "worker_read_write_locks" if read_write else "worker_locks"
 
-        self._looping_call = clock.looping_call(
-            self._renew,
-            _RENEWAL_INTERVAL_MS,
-            store,
-            clock,
-            read_write,
-            lock_name,
-            lock_key,
-            token,
-        )
+        # We might be called from a non-main thread, so we defer setting up the
+        # looping call.
+        self._looping_call: Optional[LoopingCall] = None
+        reactor.callFromThread(self._setup_looping_call)
 
         self._dropped = False
 
+    def _setup_looping_call(self) -> None:
+        self._looping_call = self._clock.looping_call(
+            self._renew,
+            _RENEWAL_INTERVAL_MS,
+            self._store,
+            self._clock,
+            self._read_write,
+            self._lock_name,
+            self._lock_key,
+            self._token,
+        )
+
     @staticmethod
     @wrap_as_background_process("Lock._renew")
     async def _renew(
@@ -459,7 +466,7 @@ class Lock:
         if self._dropped:
             return
 
-        if self._looping_call.running:
+        if self._looping_call and self._looping_call.running:
             self._looping_call.stop()
 
         await self._store.db_pool.simple_delete(
@@ -486,8 +493,9 @@ class Lock:
             # We should not be dropped without the lock being released (unless
             # we're shutting down), but if we are then let's at least stop
             # renewing the lock.
-            if self._looping_call.running:
-                self._looping_call.stop()
+            if self._looping_call and self._looping_call.running:
+                # We might be called from a non-main thread.
+                self._reactor.callFromThread(self._looping_call.stop)
 
             if self._reactor.running:
                 logger.error(
diff --git a/synapse/storage/databases/main/push_rule.py b/synapse/storage/databases/main/push_rule.py
index c13c0bc7d7..bec0dc2afe 100644
--- a/synapse/storage/databases/main/push_rule.py
+++ b/synapse/storage/databases/main/push_rule.py
@@ -88,7 +88,6 @@ def _load_rules(
         msc1767_enabled=experimental_config.msc1767_enabled,
         msc3664_enabled=experimental_config.msc3664_enabled,
         msc3381_polls_enabled=experimental_config.msc3381_polls_enabled,
-        msc3958_suppress_edits_enabled=experimental_config.msc3958_supress_edit_notifs,
     )
 
     return filtered_rules
diff --git a/synapse/storage/databases/main/registration.py b/synapse/storage/databases/main/registration.py
index d3a01d526f..7e85b73e8e 100644
--- a/synapse/storage/databases/main/registration.py
+++ b/synapse/storage/databases/main/registration.py
@@ -206,8 +206,12 @@ class RegistrationWorkerStore(CacheInvalidationWorkerStore):
                     consent_server_notice_sent, appservice_id, creation_ts, user_type,
                     deactivated, COALESCE(shadow_banned, FALSE) AS shadow_banned,
                     COALESCE(approved, TRUE) AS approved,
-                    COALESCE(locked, FALSE) AS locked
+                    COALESCE(locked, FALSE) AS locked, last_seen_ts
                 FROM users
+                LEFT JOIN (
+                    SELECT user_id, MAX(last_seen) AS last_seen_ts
+                    FROM user_ips GROUP BY user_id
+                ) ls ON users.name = ls.user_id
                 WHERE name = ?
                 """,
                 (user_id,),
@@ -268,6 +272,7 @@ class RegistrationWorkerStore(CacheInvalidationWorkerStore):
             is_shadow_banned=bool(user_data["shadow_banned"]),
             user_id=UserID.from_string(user_data["name"]),
             user_type=user_data["user_type"],
+            last_seen_ts=user_data["last_seen_ts"],
         )
 
     async def is_trial_user(self, user_id: str) -> bool:
diff --git a/synapse/storage/databases/main/stats.py b/synapse/storage/databases/main/stats.py
index 6298f0984d..3a2966b9e4 100644
--- a/synapse/storage/databases/main/stats.py
+++ b/synapse/storage/databases/main/stats.py
@@ -107,6 +107,7 @@ class UserSortOrder(Enum):
     AVATAR_URL = "avatar_url"
     SHADOW_BANNED = "shadow_banned"
     CREATION_TS = "creation_ts"
+    LAST_SEEN_TS = "last_seen_ts"
 
 
 class StatsStore(StateDeltasStore):
diff --git a/synapse/storage/databases/main/transactions.py b/synapse/storage/databases/main/transactions.py
index 860bbf7c0f..efd21b5bfc 100644
--- a/synapse/storage/databases/main/transactions.py
+++ b/synapse/storage/databases/main/transactions.py
@@ -14,7 +14,7 @@
 
 import logging
 from enum import Enum
-from typing import TYPE_CHECKING, Iterable, List, Optional, Tuple, cast
+from typing import TYPE_CHECKING, Dict, Iterable, List, Optional, Tuple, cast
 
 import attr
 from canonicaljson import encode_canonical_json
@@ -28,8 +28,8 @@ from synapse.storage.database import (
     LoggingTransaction,
 )
 from synapse.storage.databases.main.cache import CacheInvalidationWorkerStore
-from synapse.types import JsonDict
-from synapse.util.caches.descriptors import cached
+from synapse.types import JsonDict, StrCollection
+from synapse.util.caches.descriptors import cached, cachedList
 
 if TYPE_CHECKING:
     from synapse.server import HomeServer
@@ -205,6 +205,26 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
         else:
             return None
 
+    @cachedList(
+        cached_method_name="get_destination_retry_timings", list_name="destinations"
+    )
+    async def get_destination_retry_timings_batch(
+        self, destinations: StrCollection
+    ) -> Dict[str, Optional[DestinationRetryTimings]]:
+        rows = await self.db_pool.simple_select_many_batch(
+            table="destinations",
+            iterable=destinations,
+            column="destination",
+            retcols=("destination", "failure_ts", "retry_last_ts", "retry_interval"),
+            desc="get_destination_retry_timings_batch",
+        )
+
+        return {
+            row.pop("destination"): DestinationRetryTimings(**row)
+            for row in rows
+            if row["retry_last_ts"] and row["failure_ts"] and row["retry_interval"]
+        }
+
     async def set_destination_retry_timings(
         self,
         destination: str,
diff --git a/synapse/storage/schema/__init__.py b/synapse/storage/schema/__init__.py
index 649d3c8e9f..422f11f59e 100644
--- a/synapse/storage/schema/__init__.py
+++ b/synapse/storage/schema/__init__.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
-SCHEMA_VERSION = 80  # remember to update the list below when updating
+SCHEMA_VERSION = 81  # remember to update the list below when updating
 """Represents the expectations made by the codebase about the database schema
 
 This should be incremented whenever the codebase changes its requirements on the
@@ -114,19 +114,15 @@ Changes in SCHEMA_VERSION = 79
 Changes in SCHEMA_VERSION = 80
     - The event_txn_id_device_id is always written to for new events.
     - Add tables for the task scheduler.
+
+Changes in SCHEMA_VERSION = 81
+    - The event_txn_id is no longer written to for new events.
 """
 
 
 SCHEMA_COMPAT_VERSION = (
-    # Queries against `event_stream_ordering` columns in membership tables must
-    # be disambiguated.
-    #
-    # The threads_id column must written to with non-null values for the
-    # event_push_actions, event_push_actions_staging, and event_push_summary tables.
-    #
-    # insertions to the column `full_user_id` of tables profiles and user_filters can no
-    # longer be null
-    76
+    # The `event_txn_id_device_id` must be written to for new events.
+    80
 )
 """Limit on how far the synapse codebase can be rolled back without breaking db compat
 
diff --git a/synapse/types/__init__.py b/synapse/types/__init__.py
index e750417189..488714f60c 100644
--- a/synapse/types/__init__.py
+++ b/synapse/types/__init__.py
@@ -946,6 +946,7 @@ class UserInfo:
         is_guest:  True if the user is a guest user.
         is_shadow_banned:  True if the user has been shadow-banned.
         user_type:  User type (None for normal user, 'support' and 'bot' other options).
+        last_seen_ts:  Last activity timestamp of the user.
     """
 
     user_id: UserID
@@ -958,6 +959,7 @@ class UserInfo:
     is_deactivated: bool
     is_guest: bool
     is_shadow_banned: bool
+    last_seen_ts: Optional[int]
 
 
 class UserProfile(TypedDict):
diff --git a/synapse/util/caches/deferred_cache.py b/synapse/util/caches/deferred_cache.py
index bf7bd351e0..029eedcc6f 100644
--- a/synapse/util/caches/deferred_cache.py
+++ b/synapse/util/caches/deferred_cache.py
@@ -470,7 +470,7 @@ class CacheMultipleEntries(CacheEntry[KT, VT]):
     def deferred(self, key: KT) -> "defer.Deferred[VT]":
         if not self._deferred:
             self._deferred = ObservableDeferred(defer.Deferred(), consumeErrors=True)
-        return self._deferred.observe().addCallback(lambda res: res.get(key))
+        return self._deferred.observe().addCallback(lambda res: res[key])
 
     def add_invalidation_callback(
         self, key: KT, callback: Optional[Callable[[], None]]
diff --git a/synapse/util/check_dependencies.py b/synapse/util/check_dependencies.py
index 114130a08f..f7cead9e12 100644
--- a/synapse/util/check_dependencies.py
+++ b/synapse/util/check_dependencies.py
@@ -51,9 +51,9 @@ class DependencyException(Exception):
 
 
 DEV_EXTRAS = {"lint", "mypy", "test", "dev"}
-RUNTIME_EXTRAS = (
-    set(metadata.metadata(DISTRIBUTION_NAME).get_all("Provides-Extra")) - DEV_EXTRAS
-)
+ALL_EXTRAS = metadata.metadata(DISTRIBUTION_NAME).get_all("Provides-Extra")
+assert ALL_EXTRAS is not None
+RUNTIME_EXTRAS = set(ALL_EXTRAS) - DEV_EXTRAS
 VERSION = metadata.version(DISTRIBUTION_NAME)
 
 
diff --git a/synapse/util/ratelimitutils.py b/synapse/util/ratelimitutils.py
index cde4a0780f..f693ba2a8c 100644
--- a/synapse/util/ratelimitutils.py
+++ b/synapse/util/ratelimitutils.py
@@ -291,7 +291,8 @@ class _PerHostRatelimiter:
             if self.metrics_name:
                 rate_limit_reject_counter.labels(self.metrics_name).inc()
             raise LimitExceededError(
-                retry_after_ms=int(self.window_size / self.sleep_limit)
+                limiter_name="rc_federation",
+                retry_after_ms=int(self.window_size / self.sleep_limit),
             )
 
         self.request_times.append(time_now)
diff --git a/synapse/util/retryutils.py b/synapse/util/retryutils.py
index 27e9fc976c..0e1f907667 100644
--- a/synapse/util/retryutils.py
+++ b/synapse/util/retryutils.py
@@ -19,6 +19,7 @@ from typing import TYPE_CHECKING, Any, Optional, Type
 from synapse.api.errors import CodeMessageException
 from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.storage import DataStore
+from synapse.types import StrCollection
 from synapse.util import Clock
 
 if TYPE_CHECKING:
@@ -116,6 +117,30 @@ async def get_retry_limiter(
     )
 
 
+async def filter_destinations_by_retry_limiter(
+    destinations: StrCollection,
+    clock: Clock,
+    store: DataStore,
+    retry_due_within_ms: int = 0,
+) -> StrCollection:
+    """Filter down the list of destinations to only those that will are either
+    alive or due for a retry (within `retry_due_within_ms`)
+    """
+    if not destinations:
+        return destinations
+
+    retry_timings = await store.get_destination_retry_timings_batch(destinations)
+
+    now = int(clock.time_msec())
+
+    return [
+        destination
+        for destination, timings in retry_timings.items()
+        if timings is None
+        or timings.retry_last_ts + timings.retry_interval <= now + retry_due_within_ms
+    ]
+
+
 class RetryDestinationLimiter:
     def __init__(
         self,
@@ -128,6 +153,7 @@ class RetryDestinationLimiter:
         backoff_on_failure: bool = True,
         notifier: Optional["Notifier"] = None,
         replication_client: Optional["ReplicationCommandHandler"] = None,
+        backoff_on_all_error_codes: bool = False,
     ):
         """Marks the destination as "down" if an exception is thrown in the
         context, except for CodeMessageException with code < 500.
@@ -147,6 +173,9 @@ class RetryDestinationLimiter:
 
             backoff_on_failure: set to False if we should not increase the
                 retry interval on a failure.
+
+            backoff_on_all_error_codes: Whether we should back off on any
+                error code.
         """
         self.clock = clock
         self.store = store
@@ -156,6 +185,7 @@ class RetryDestinationLimiter:
         self.retry_interval = retry_interval
         self.backoff_on_404 = backoff_on_404
         self.backoff_on_failure = backoff_on_failure
+        self.backoff_on_all_error_codes = backoff_on_all_error_codes
 
         self.notifier = notifier
         self.replication_client = replication_client
@@ -179,6 +209,7 @@ class RetryDestinationLimiter:
         exc_val: Optional[BaseException],
         exc_tb: Optional[TracebackType],
     ) -> None:
+        success = exc_type is None
         valid_err_code = False
         if exc_type is None:
             valid_err_code = True
@@ -195,7 +226,9 @@ class RetryDestinationLimiter:
             # won't accept our requests for at least a while.
             # 429 is us being aggressively rate limited, so lets rate limit
             # ourselves.
-            if exc_val.code == 404 and self.backoff_on_404:
+            if self.backoff_on_all_error_codes:
+                valid_err_code = False
+            elif exc_val.code == 404 and self.backoff_on_404:
                 valid_err_code = False
             elif exc_val.code in (401, 429):
                 valid_err_code = False
@@ -204,7 +237,7 @@ class RetryDestinationLimiter:
             else:
                 valid_err_code = False
 
-        if valid_err_code:
+        if success:
             # We connected successfully.
             if not self.retry_interval:
                 return
@@ -215,6 +248,12 @@ class RetryDestinationLimiter:
             self.failure_ts = None
             retry_last_ts = 0
             self.retry_interval = 0
+        elif valid_err_code:
+            # We got a potentially valid error code back. We don't reset the
+            # timers though, as the other side might actually be down anyway
+            # (e.g. some deprovisioned servers will always return a 404 or 403,
+            # and we don't want to keep resetting the retry timers for them).
+            return
         elif not self.backoff_on_failure:
             return
         else:
diff --git a/synapse/util/task_scheduler.py b/synapse/util/task_scheduler.py
index 4aea64b338..9e89aeb748 100644
--- a/synapse/util/task_scheduler.py
+++ b/synapse/util/task_scheduler.py
@@ -57,14 +57,13 @@ class TaskScheduler:
     the code launching the task.
     You can also specify the `result` (and/or an `error`) when returning from the function.
 
-    The reconciliation loop runs every 5 mns, so this is not a precise scheduler. When wanting
-    to launch now, the launch will still not happen before the next loop run.
-
-    Tasks will be run on the worker specified with `run_background_tasks_on` config,
-    or the main one by default.
+    The reconciliation loop runs every minute, so this is not a precise scheduler.
     There is a limit of 10 concurrent tasks, so tasks may be delayed if the pool is already
     full. In this regard, please take great care that scheduled tasks can actually finished.
     For now there is no mechanism to stop a running task if it is stuck.
+
+    Tasks will be run on the worker specified with `run_background_tasks_on` config,
+    or the main one by default.
     """
 
     # Precision of the scheduler, evaluation of tasks to run will only happen
@@ -85,7 +84,7 @@ class TaskScheduler:
         self._actions: Dict[
             str,
             Callable[
-                [ScheduledTask, bool],
+                [ScheduledTask],
                 Awaitable[Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]],
             ],
         ] = {}
@@ -98,11 +97,13 @@ class TaskScheduler:
                 "handle_scheduled_tasks",
                 self._handle_scheduled_tasks,
             )
+        else:
+            self.replication_client = hs.get_replication_command_handler()
 
     def register_action(
         self,
         function: Callable[
-            [ScheduledTask, bool],
+            [ScheduledTask],
             Awaitable[Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]],
         ],
         action_name: str,
@@ -115,10 +116,9 @@ class TaskScheduler:
         calling `schedule_task` but rather in an `__init__` method.
 
         Args:
-            function: The function to be executed for this action. The parameters
-                passed to the function when launched are the `ScheduledTask` being run,
-                and a `first_launch` boolean to signal if it's a resumed task or the first
-                launch of it. The function should return a tuple of new `status`, `result`
+            function: The function to be executed for this action. The parameter
+                passed to the function when launched is the `ScheduledTask` being run.
+                The function should return a tuple of new `status`, `result`
                 and `error` as specified in `ScheduledTask`.
             action_name: The name of the action to be associated with the function
         """
@@ -171,6 +171,12 @@ class TaskScheduler:
         )
         await self._store.insert_scheduled_task(task)
 
+        if status == TaskStatus.ACTIVE:
+            if self._run_background_tasks:
+                await self._launch_task(task)
+            else:
+                self.replication_client.send_new_active_task(task.id)
+
         return task.id
 
     async def update_task(
@@ -265,21 +271,13 @@ class TaskScheduler:
         Args:
             id: id of the task to delete
         """
-        if self.task_is_running(id):
-            raise Exception(f"Task {id} is currently running and can't be deleted")
+        task = await self.get_task(id)
+        if task is None:
+            raise Exception(f"Task {id} does not exist")
+        if task.status == TaskStatus.ACTIVE:
+            raise Exception(f"Task {id} is currently ACTIVE and can't be deleted")
         await self._store.delete_scheduled_task(id)
 
-    def task_is_running(self, id: str) -> bool:
-        """Check if a task is currently running.
-
-        Can only be called from the worker handling the task scheduling.
-
-        Args:
-            id: id of the task to check
-        """
-        assert self._run_background_tasks
-        return id in self._running_tasks
-
     async def _handle_scheduled_tasks(self) -> None:
         """Main loop taking care of launching tasks and cleaning up old ones."""
         await self._launch_scheduled_tasks()
@@ -288,29 +286,11 @@ class TaskScheduler:
     async def _launch_scheduled_tasks(self) -> None:
         """Retrieve and launch scheduled tasks that should be running at that time."""
         for task in await self.get_tasks(statuses=[TaskStatus.ACTIVE]):
-            if not self.task_is_running(task.id):
-                if (
-                    len(self._running_tasks)
-                    < TaskScheduler.MAX_CONCURRENT_RUNNING_TASKS
-                ):
-                    await self._launch_task(task, first_launch=False)
-            else:
-                if (
-                    self._clock.time_msec()
-                    > task.timestamp + TaskScheduler.LAST_UPDATE_BEFORE_WARNING_MS
-                ):
-                    logger.warn(
-                        f"Task {task.id} (action {task.action}) has seen no update for more than 24h and may be stuck"
-                    )
+            await self._launch_task(task)
         for task in await self.get_tasks(
             statuses=[TaskStatus.SCHEDULED], max_timestamp=self._clock.time_msec()
         ):
-            if (
-                not self.task_is_running(task.id)
-                and len(self._running_tasks)
-                < TaskScheduler.MAX_CONCURRENT_RUNNING_TASKS
-            ):
-                await self._launch_task(task, first_launch=True)
+            await self._launch_task(task)
 
         running_tasks_gauge.set(len(self._running_tasks))
 
@@ -320,27 +300,27 @@ class TaskScheduler:
             statuses=[TaskStatus.FAILED, TaskStatus.COMPLETE]
         ):
             # FAILED and COMPLETE tasks should never be running
-            assert not self.task_is_running(task.id)
+            assert task.id not in self._running_tasks
             if (
                 self._clock.time_msec()
                 > task.timestamp + TaskScheduler.KEEP_TASKS_FOR_MS
             ):
                 await self._store.delete_scheduled_task(task.id)
 
-    async def _launch_task(self, task: ScheduledTask, first_launch: bool) -> None:
+    async def _launch_task(self, task: ScheduledTask) -> None:
         """Launch a scheduled task now.
 
         Args:
             task: the task to launch
-            first_launch: `True` if it's the first time is launched, `False` otherwise
         """
-        assert task.action in self._actions
+        assert self._run_background_tasks
 
+        assert task.action in self._actions
         function = self._actions[task.action]
 
         async def wrapper() -> None:
             try:
-                (status, result, error) = await function(task, first_launch)
+                (status, result, error) = await function(task)
             except Exception:
                 f = Failure()
                 logger.error(
@@ -360,6 +340,20 @@ class TaskScheduler:
             )
             self._running_tasks.remove(task.id)
 
+        if len(self._running_tasks) >= TaskScheduler.MAX_CONCURRENT_RUNNING_TASKS:
+            return
+
+        if (
+            self._clock.time_msec()
+            > task.timestamp + TaskScheduler.LAST_UPDATE_BEFORE_WARNING_MS
+        ):
+            logger.warn(
+                f"Task {task.id} (action {task.action}) has seen no update for more than 24h and may be stuck"
+            )
+
+        if task.id in self._running_tasks:
+            return
+
         self._running_tasks.add(task.id)
         await self.update_task(task.id, status=TaskStatus.ACTIVE)
         description = f"{task.id}-{task.action}"
diff --git a/tests/api/test_auth.py b/tests/api/test_auth.py
index ce96574915..dcd01d5688 100644
--- a/tests/api/test_auth.py
+++ b/tests/api/test_auth.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 import pymacaroons
 
@@ -35,7 +35,6 @@ from synapse.types import Requester, UserID
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import simple_async_mock
 from tests.unittest import override_config
 from tests.utils import mock_getRawHeaders
 
@@ -60,16 +59,16 @@ class AuthTestCase(unittest.HomeserverTestCase):
         # this is overridden for the appservice tests
         self.store.get_app_service_by_token = Mock(return_value=None)
 
-        self.store.insert_client_ip = simple_async_mock(None)
-        self.store.is_support_user = simple_async_mock(False)
+        self.store.insert_client_ip = AsyncMock(return_value=None)
+        self.store.is_support_user = AsyncMock(return_value=False)
 
     def test_get_user_by_req_user_valid_token(self) -> None:
         user_info = TokenLookupResult(
             user_id=self.test_user, token_id=5, device_id="device"
         )
-        self.store.get_user_by_access_token = simple_async_mock(user_info)
-        self.store.mark_access_token_as_used = simple_async_mock(None)
-        self.store.get_user_locked_status = simple_async_mock(False)
+        self.store.get_user_by_access_token = AsyncMock(return_value=user_info)
+        self.store.mark_access_token_as_used = AsyncMock(return_value=None)
+        self.store.get_user_locked_status = AsyncMock(return_value=False)
 
         request = Mock(args={})
         request.args[b"access_token"] = [self.test_token]
@@ -78,7 +77,7 @@ class AuthTestCase(unittest.HomeserverTestCase):
         self.assertEqual(requester.user.to_string(), self.test_user)
 
     def test_get_user_by_req_user_bad_token(self) -> None:
-        self.store.get_user_by_access_token = simple_async_mock(None)
+        self.store.get_user_by_access_token = AsyncMock(return_value=None)
 
         request = Mock(args={})
         request.args[b"access_token"] = [self.test_token]
@@ -91,7 +90,7 @@ class AuthTestCase(unittest.HomeserverTestCase):
 
     def test_get_user_by_req_user_missing_token(self) -> None:
         user_info = TokenLookupResult(user_id=self.test_user, token_id=5)
-        self.store.get_user_by_access_token = simple_async_mock(user_info)
+        self.store.get_user_by_access_token = AsyncMock(return_value=user_info)
 
         request = Mock(args={})
         request.requestHeaders.getRawHeaders = mock_getRawHeaders()
@@ -106,7 +105,7 @@ class AuthTestCase(unittest.HomeserverTestCase):
             token="foobar", url="a_url", sender=self.test_user, ip_range_whitelist=None
         )
         self.store.get_app_service_by_token = Mock(return_value=app_service)
-        self.store.get_user_by_access_token = simple_async_mock(None)
+        self.store.get_user_by_access_token = AsyncMock(return_value=None)
 
         request = Mock(args={})
         request.getClientAddress.return_value.host = "127.0.0.1"
@@ -125,7 +124,7 @@ class AuthTestCase(unittest.HomeserverTestCase):
             ip_range_whitelist=IPSet(["192.168/16"]),
         )
         self.store.get_app_service_by_token = Mock(return_value=app_service)
-        self.store.get_user_by_access_token = simple_async_mock(None)
+        self.store.get_user_by_access_token = AsyncMock(return_value=None)
 
         request = Mock(args={})
         request.getClientAddress.return_value.host = "192.168.10.10"
@@ -144,7 +143,7 @@ class AuthTestCase(unittest.HomeserverTestCase):
             ip_range_whitelist=IPSet(["192.168/16"]),
         )
         self.store.get_app_service_by_token = Mock(return_value=app_service)
-        self.store.get_user_by_access_token = simple_async_mock(None)
+        self.store.get_user_by_access_token = AsyncMock(return_value=None)
 
         request = Mock(args={})
         request.getClientAddress.return_value.host = "131.111.8.42"
@@ -158,7 +157,7 @@ class AuthTestCase(unittest.HomeserverTestCase):
 
     def test_get_user_by_req_appservice_bad_token(self) -> None:
         self.store.get_app_service_by_token = Mock(return_value=None)
-        self.store.get_user_by_access_token = simple_async_mock(None)
+        self.store.get_user_by_access_token = AsyncMock(return_value=None)
 
         request = Mock(args={})
         request.args[b"access_token"] = [self.test_token]
@@ -172,7 +171,7 @@ class AuthTestCase(unittest.HomeserverTestCase):
     def test_get_user_by_req_appservice_missing_token(self) -> None:
         app_service = Mock(token="foobar", url="a_url", sender=self.test_user)
         self.store.get_app_service_by_token = Mock(return_value=app_service)
-        self.store.get_user_by_access_token = simple_async_mock(None)
+        self.store.get_user_by_access_token = AsyncMock(return_value=None)
 
         request = Mock(args={})
         request.requestHeaders.getRawHeaders = mock_getRawHeaders()
@@ -190,8 +189,8 @@ class AuthTestCase(unittest.HomeserverTestCase):
         app_service.is_interested_in_user = Mock(return_value=True)
         self.store.get_app_service_by_token = Mock(return_value=app_service)
         # This just needs to return a truth-y value.
-        self.store.get_user_by_id = simple_async_mock({"is_guest": False})
-        self.store.get_user_by_access_token = simple_async_mock(None)
+        self.store.get_user_by_id = AsyncMock(return_value={"is_guest": False})
+        self.store.get_user_by_access_token = AsyncMock(return_value=None)
 
         request = Mock(args={})
         request.getClientAddress.return_value.host = "127.0.0.1"
@@ -210,7 +209,7 @@ class AuthTestCase(unittest.HomeserverTestCase):
         )
         app_service.is_interested_in_user = Mock(return_value=False)
         self.store.get_app_service_by_token = Mock(return_value=app_service)
-        self.store.get_user_by_access_token = simple_async_mock(None)
+        self.store.get_user_by_access_token = AsyncMock(return_value=None)
 
         request = Mock(args={})
         request.getClientAddress.return_value.host = "127.0.0.1"
@@ -234,10 +233,10 @@ class AuthTestCase(unittest.HomeserverTestCase):
         app_service.is_interested_in_user = Mock(return_value=True)
         self.store.get_app_service_by_token = Mock(return_value=app_service)
         # This just needs to return a truth-y value.
-        self.store.get_user_by_id = simple_async_mock({"is_guest": False})
-        self.store.get_user_by_access_token = simple_async_mock(None)
+        self.store.get_user_by_id = AsyncMock(return_value={"is_guest": False})
+        self.store.get_user_by_access_token = AsyncMock(return_value=None)
         # This also needs to just return a truth-y value
-        self.store.get_device = simple_async_mock({"hidden": False})
+        self.store.get_device = AsyncMock(return_value={"hidden": False})
 
         request = Mock(args={})
         request.getClientAddress.return_value.host = "127.0.0.1"
@@ -266,10 +265,10 @@ class AuthTestCase(unittest.HomeserverTestCase):
         app_service.is_interested_in_user = Mock(return_value=True)
         self.store.get_app_service_by_token = Mock(return_value=app_service)
         # This just needs to return a truth-y value.
-        self.store.get_user_by_id = simple_async_mock({"is_guest": False})
-        self.store.get_user_by_access_token = simple_async_mock(None)
+        self.store.get_user_by_id = AsyncMock(return_value={"is_guest": False})
+        self.store.get_user_by_access_token = AsyncMock(return_value=None)
         # This also needs to just return a falsey value
-        self.store.get_device = simple_async_mock(None)
+        self.store.get_device = AsyncMock(return_value=None)
 
         request = Mock(args={})
         request.getClientAddress.return_value.host = "127.0.0.1"
@@ -283,8 +282,8 @@ class AuthTestCase(unittest.HomeserverTestCase):
         self.assertEqual(failure.value.errcode, Codes.EXCLUSIVE)
 
     def test_get_user_by_req__puppeted_token__not_tracking_puppeted_mau(self) -> None:
-        self.store.get_user_by_access_token = simple_async_mock(
-            TokenLookupResult(
+        self.store.get_user_by_access_token = AsyncMock(
+            return_value=TokenLookupResult(
                 user_id="@baldrick:matrix.org",
                 device_id="device",
                 token_id=5,
@@ -292,9 +291,9 @@ class AuthTestCase(unittest.HomeserverTestCase):
                 token_used=True,
             )
         )
-        self.store.insert_client_ip = simple_async_mock(None)
-        self.store.mark_access_token_as_used = simple_async_mock(None)
-        self.store.get_user_locked_status = simple_async_mock(False)
+        self.store.insert_client_ip = AsyncMock(return_value=None)
+        self.store.mark_access_token_as_used = AsyncMock(return_value=None)
+        self.store.get_user_locked_status = AsyncMock(return_value=False)
         request = Mock(args={})
         request.getClientAddress.return_value.host = "127.0.0.1"
         request.args[b"access_token"] = [self.test_token]
@@ -304,8 +303,8 @@ class AuthTestCase(unittest.HomeserverTestCase):
 
     def test_get_user_by_req__puppeted_token__tracking_puppeted_mau(self) -> None:
         self.auth._track_puppeted_user_ips = True
-        self.store.get_user_by_access_token = simple_async_mock(
-            TokenLookupResult(
+        self.store.get_user_by_access_token = AsyncMock(
+            return_value=TokenLookupResult(
                 user_id="@baldrick:matrix.org",
                 device_id="device",
                 token_id=5,
@@ -313,9 +312,9 @@ class AuthTestCase(unittest.HomeserverTestCase):
                 token_used=True,
             )
         )
-        self.store.get_user_locked_status = simple_async_mock(False)
-        self.store.insert_client_ip = simple_async_mock(None)
-        self.store.mark_access_token_as_used = simple_async_mock(None)
+        self.store.get_user_locked_status = AsyncMock(return_value=False)
+        self.store.insert_client_ip = AsyncMock(return_value=None)
+        self.store.mark_access_token_as_used = AsyncMock(return_value=None)
         request = Mock(args={})
         request.getClientAddress.return_value.host = "127.0.0.1"
         request.args[b"access_token"] = [self.test_token]
@@ -324,7 +323,7 @@ class AuthTestCase(unittest.HomeserverTestCase):
         self.assertEqual(self.store.insert_client_ip.call_count, 2)
 
     def test_get_user_from_macaroon(self) -> None:
-        self.store.get_user_by_access_token = simple_async_mock(None)
+        self.store.get_user_by_access_token = AsyncMock(return_value=None)
 
         user_id = "@baldrick:matrix.org"
         macaroon = pymacaroons.Macaroon(
@@ -342,8 +341,8 @@ class AuthTestCase(unittest.HomeserverTestCase):
         )
 
     def test_get_guest_user_from_macaroon(self) -> None:
-        self.store.get_user_by_id = simple_async_mock({"is_guest": True})
-        self.store.get_user_by_access_token = simple_async_mock(None)
+        self.store.get_user_by_id = AsyncMock(return_value={"is_guest": True})
+        self.store.get_user_by_access_token = AsyncMock(return_value=None)
 
         user_id = "@baldrick:matrix.org"
         macaroon = pymacaroons.Macaroon(
@@ -373,7 +372,7 @@ class AuthTestCase(unittest.HomeserverTestCase):
 
         self.auth_blocking._limit_usage_by_mau = True
 
-        self.store.get_monthly_active_count = simple_async_mock(lots_of_users)
+        self.store.get_monthly_active_count = AsyncMock(return_value=lots_of_users)
 
         e = self.get_failure(
             self.auth_blocking.check_auth_blocking(), ResourceLimitError
@@ -383,25 +382,27 @@ class AuthTestCase(unittest.HomeserverTestCase):
         self.assertEqual(e.value.code, 403)
 
         # Ensure does not throw an error
-        self.store.get_monthly_active_count = simple_async_mock(small_number_of_users)
+        self.store.get_monthly_active_count = AsyncMock(
+            return_value=small_number_of_users
+        )
         self.get_success(self.auth_blocking.check_auth_blocking())
 
     def test_blocking_mau__depending_on_user_type(self) -> None:
         self.auth_blocking._max_mau_value = 50
         self.auth_blocking._limit_usage_by_mau = True
 
-        self.store.get_monthly_active_count = simple_async_mock(100)
+        self.store.get_monthly_active_count = AsyncMock(return_value=100)
         # Support users allowed
         self.get_success(
             self.auth_blocking.check_auth_blocking(user_type=UserTypes.SUPPORT)
         )
-        self.store.get_monthly_active_count = simple_async_mock(100)
+        self.store.get_monthly_active_count = AsyncMock(return_value=100)
         # Bots not allowed
         self.get_failure(
             self.auth_blocking.check_auth_blocking(user_type=UserTypes.BOT),
             ResourceLimitError,
         )
-        self.store.get_monthly_active_count = simple_async_mock(100)
+        self.store.get_monthly_active_count = AsyncMock(return_value=100)
         # Real users not allowed
         self.get_failure(self.auth_blocking.check_auth_blocking(), ResourceLimitError)
 
@@ -412,9 +413,9 @@ class AuthTestCase(unittest.HomeserverTestCase):
         self.auth_blocking._limit_usage_by_mau = True
         self.auth_blocking._track_appservice_user_ips = False
 
-        self.store.get_monthly_active_count = simple_async_mock(100)
-        self.store.user_last_seen_monthly_active = simple_async_mock()
-        self.store.is_trial_user = simple_async_mock()
+        self.store.get_monthly_active_count = AsyncMock(return_value=100)
+        self.store.user_last_seen_monthly_active = AsyncMock(return_value=None)
+        self.store.is_trial_user = AsyncMock(return_value=False)
 
         appservice = ApplicationService(
             "abcd",
@@ -443,9 +444,9 @@ class AuthTestCase(unittest.HomeserverTestCase):
         self.auth_blocking._limit_usage_by_mau = True
         self.auth_blocking._track_appservice_user_ips = True
 
-        self.store.get_monthly_active_count = simple_async_mock(100)
-        self.store.user_last_seen_monthly_active = simple_async_mock()
-        self.store.is_trial_user = simple_async_mock()
+        self.store.get_monthly_active_count = AsyncMock(return_value=100)
+        self.store.user_last_seen_monthly_active = AsyncMock(return_value=None)
+        self.store.is_trial_user = AsyncMock(return_value=False)
 
         appservice = ApplicationService(
             "abcd",
@@ -473,7 +474,7 @@ class AuthTestCase(unittest.HomeserverTestCase):
     def test_reserved_threepid(self) -> None:
         self.auth_blocking._limit_usage_by_mau = True
         self.auth_blocking._max_mau_value = 1
-        self.store.get_monthly_active_count = simple_async_mock(2)
+        self.store.get_monthly_active_count = AsyncMock(return_value=2)
         threepid = {"medium": "email", "address": "reserved@server.com"}
         unknown_threepid = {"medium": "email", "address": "unreserved@server.com"}
         self.auth_blocking._mau_limits_reserved_threepids = [threepid]
diff --git a/tests/api/test_errors.py b/tests/api/test_errors.py
new file mode 100644
index 0000000000..8e159029d9
--- /dev/null
+++ b/tests/api/test_errors.py
@@ -0,0 +1,43 @@
+# Copyright 2023 The Matrix.org Foundation C.I.C.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+import json
+
+from synapse.api.errors import LimitExceededError
+
+from tests import unittest
+
+
+class LimitExceededErrorTestCase(unittest.TestCase):
+    def test_key_appears_in_context_but_not_error_dict(self) -> None:
+        err = LimitExceededError("needle")
+        serialised = json.dumps(err.error_dict(None))
+        self.assertIn("needle", err.debug_context)
+        self.assertNotIn("needle", serialised)
+
+    # Create a sub-class to avoid mutating the class-level property.
+    class LimitExceededErrorHeaders(LimitExceededError):
+        include_retry_after_header = True
+
+    def test_limit_exceeded_header(self) -> None:
+        err = self.LimitExceededErrorHeaders(limiter_name="test", retry_after_ms=100)
+        self.assertEqual(err.error_dict(None).get("retry_after_ms"), 100)
+        assert err.headers is not None
+        self.assertEqual(err.headers.get("Retry-After"), "1")
+
+    def test_limit_exceeded_rounding(self) -> None:
+        err = self.LimitExceededErrorHeaders(limiter_name="test", retry_after_ms=3001)
+        self.assertEqual(err.error_dict(None).get("retry_after_ms"), 3001)
+        assert err.headers is not None
+        self.assertEqual(err.headers.get("Retry-After"), "4")
diff --git a/tests/api/test_ratelimiting.py b/tests/api/test_ratelimiting.py
index fa6c1c02ce..a24638c9ef 100644
--- a/tests/api/test_ratelimiting.py
+++ b/tests/api/test_ratelimiting.py
@@ -1,5 +1,6 @@
 from synapse.api.ratelimiting import LimitExceededError, Ratelimiter
 from synapse.appservice import ApplicationService
+from synapse.config.ratelimiting import RatelimitSettings
 from synapse.types import create_requester
 
 from tests import unittest
@@ -10,8 +11,7 @@ class TestRatelimiter(unittest.HomeserverTestCase):
         limiter = Ratelimiter(
             store=self.hs.get_datastores().main,
             clock=self.clock,
-            rate_hz=0.1,
-            burst_count=1,
+            cfg=RatelimitSettings(key="", per_second=0.1, burst_count=1),
         )
         allowed, time_allowed = self.get_success_or_raise(
             limiter.can_do_action(None, key="test_id", _time_now_s=0)
@@ -43,8 +43,11 @@ class TestRatelimiter(unittest.HomeserverTestCase):
         limiter = Ratelimiter(
             store=self.hs.get_datastores().main,
             clock=self.clock,
-            rate_hz=0.1,
-            burst_count=1,
+            cfg=RatelimitSettings(
+                key="",
+                per_second=0.1,
+                burst_count=1,
+            ),
         )
         allowed, time_allowed = self.get_success_or_raise(
             limiter.can_do_action(as_requester, _time_now_s=0)
@@ -76,8 +79,11 @@ class TestRatelimiter(unittest.HomeserverTestCase):
         limiter = Ratelimiter(
             store=self.hs.get_datastores().main,
             clock=self.clock,
-            rate_hz=0.1,
-            burst_count=1,
+            cfg=RatelimitSettings(
+                key="",
+                per_second=0.1,
+                burst_count=1,
+            ),
         )
         allowed, time_allowed = self.get_success_or_raise(
             limiter.can_do_action(as_requester, _time_now_s=0)
@@ -101,8 +107,7 @@ class TestRatelimiter(unittest.HomeserverTestCase):
         limiter = Ratelimiter(
             store=self.hs.get_datastores().main,
             clock=self.clock,
-            rate_hz=0.1,
-            burst_count=1,
+            cfg=RatelimitSettings(key="", per_second=0.1, burst_count=1),
         )
 
         # Shouldn't raise
@@ -128,8 +133,7 @@ class TestRatelimiter(unittest.HomeserverTestCase):
         limiter = Ratelimiter(
             store=self.hs.get_datastores().main,
             clock=self.clock,
-            rate_hz=0.1,
-            burst_count=1,
+            cfg=RatelimitSettings(key="", per_second=0.1, burst_count=1),
         )
 
         # First attempt should be allowed
@@ -177,8 +181,7 @@ class TestRatelimiter(unittest.HomeserverTestCase):
         limiter = Ratelimiter(
             store=self.hs.get_datastores().main,
             clock=self.clock,
-            rate_hz=0.1,
-            burst_count=1,
+            cfg=RatelimitSettings(key="", per_second=0.1, burst_count=1),
         )
 
         # First attempt should be allowed
@@ -208,8 +211,7 @@ class TestRatelimiter(unittest.HomeserverTestCase):
         limiter = Ratelimiter(
             store=self.hs.get_datastores().main,
             clock=self.clock,
-            rate_hz=0.1,
-            burst_count=1,
+            cfg=RatelimitSettings(key="", per_second=0.1, burst_count=1),
         )
         self.get_success_or_raise(
             limiter.can_do_action(None, key="test_id_1", _time_now_s=0)
@@ -244,7 +246,11 @@ class TestRatelimiter(unittest.HomeserverTestCase):
             )
         )
 
-        limiter = Ratelimiter(store=store, clock=self.clock, rate_hz=0.1, burst_count=1)
+        limiter = Ratelimiter(
+            store=store,
+            clock=self.clock,
+            cfg=RatelimitSettings("", per_second=0.1, burst_count=1),
+        )
 
         # Shouldn't raise
         for _ in range(20):
@@ -254,8 +260,11 @@ class TestRatelimiter(unittest.HomeserverTestCase):
         limiter = Ratelimiter(
             store=self.hs.get_datastores().main,
             clock=self.clock,
-            rate_hz=0.1,
-            burst_count=3,
+            cfg=RatelimitSettings(
+                key="",
+                per_second=0.1,
+                burst_count=3,
+            ),
         )
         # Test that 4 actions aren't allowed with a maximum burst of 3.
         allowed, time_allowed = self.get_success_or_raise(
@@ -321,8 +330,7 @@ class TestRatelimiter(unittest.HomeserverTestCase):
         limiter = Ratelimiter(
             store=self.hs.get_datastores().main,
             clock=self.clock,
-            rate_hz=0.1,
-            burst_count=3,
+            cfg=RatelimitSettings("", per_second=0.1, burst_count=3),
         )
 
         def consume_at(time: float) -> bool:
@@ -346,8 +354,11 @@ class TestRatelimiter(unittest.HomeserverTestCase):
         limiter = Ratelimiter(
             store=self.hs.get_datastores().main,
             clock=self.clock,
-            rate_hz=0.1,
-            burst_count=3,
+            cfg=RatelimitSettings(
+                "",
+                per_second=0.1,
+                burst_count=3,
+            ),
         )
 
         # Observe two actions, leaving room in the bucket for one more.
@@ -369,8 +380,11 @@ class TestRatelimiter(unittest.HomeserverTestCase):
         limiter = Ratelimiter(
             store=self.hs.get_datastores().main,
             clock=self.clock,
-            rate_hz=0.1,
-            burst_count=3,
+            cfg=RatelimitSettings(
+                "",
+                per_second=0.1,
+                burst_count=3,
+            ),
         )
 
         # Observe three actions, filling up the bucket.
@@ -398,8 +412,11 @@ class TestRatelimiter(unittest.HomeserverTestCase):
         limiter = Ratelimiter(
             store=self.hs.get_datastores().main,
             clock=self.clock,
-            rate_hz=0.1,
-            burst_count=3,
+            cfg=RatelimitSettings(
+                "",
+                per_second=0.1,
+                burst_count=3,
+            ),
         )
 
         # Observe four actions, exceeding the bucket.
diff --git a/tests/appservice/test_api.py b/tests/appservice/test_api.py
index 3c635e3dcb..75fb5fae6b 100644
--- a/tests/appservice/test_api.py
+++ b/tests/appservice/test_api.py
@@ -96,7 +96,7 @@ class ApplicationServiceApiTestCase(unittest.HomeserverTestCase):
                 )
 
         # We assign to a method, which mypy doesn't like.
-        self.api.get_json = Mock(side_effect=get_json)  # type: ignore[assignment]
+        self.api.get_json = Mock(side_effect=get_json)  # type: ignore[method-assign]
 
         result = self.get_success(
             self.api.query_3pe(self.service, "user", PROTOCOL, {b"some": [b"field"]})
@@ -168,7 +168,7 @@ class ApplicationServiceApiTestCase(unittest.HomeserverTestCase):
                 )
 
         # We assign to a method, which mypy doesn't like.
-        self.api.get_json = Mock(side_effect=get_json)  # type: ignore[assignment]
+        self.api.get_json = Mock(side_effect=get_json)  # type: ignore[method-assign]
 
         result = self.get_success(
             self.api.query_3pe(self.service, "user", PROTOCOL, {b"some": [b"field"]})
@@ -215,7 +215,7 @@ class ApplicationServiceApiTestCase(unittest.HomeserverTestCase):
             return RESPONSE
 
         # We assign to a method, which mypy doesn't like.
-        self.api.post_json_get_json = Mock(side_effect=post_json_get_json)  # type: ignore[assignment]
+        self.api.post_json_get_json = Mock(side_effect=post_json_get_json)  # type: ignore[method-assign]
 
         MISSING_KEYS = [
             # Known user, known device, missing algorithm.
diff --git a/tests/appservice/test_appservice.py b/tests/appservice/test_appservice.py
index 66753c60c4..6ac5fc1ae7 100644
--- a/tests/appservice/test_appservice.py
+++ b/tests/appservice/test_appservice.py
@@ -13,14 +13,13 @@
 # limitations under the License.
 import re
 from typing import Any, Generator
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from twisted.internet import defer
 
 from synapse.appservice import ApplicationService, Namespace
 
 from tests import unittest
-from tests.test_utils import simple_async_mock
 
 
 def _regex(regex: str, exclusive: bool = True) -> Namespace:
@@ -43,8 +42,8 @@ class ApplicationServiceTestCase(unittest.TestCase):
         )
 
         self.store = Mock()
-        self.store.get_aliases_for_room = simple_async_mock([])
-        self.store.get_local_users_in_room = simple_async_mock([])
+        self.store.get_aliases_for_room = AsyncMock(return_value=[])
+        self.store.get_local_users_in_room = AsyncMock(return_value=[])
 
     @defer.inlineCallbacks
     def test_regex_user_id_prefix_match(
@@ -127,10 +126,10 @@ class ApplicationServiceTestCase(unittest.TestCase):
         self.service.namespaces[ApplicationService.NS_ALIASES].append(
             _regex("#irc_.*:matrix.org")
         )
-        self.store.get_aliases_for_room = simple_async_mock(
-            ["#irc_foobar:matrix.org", "#athing:matrix.org"]
+        self.store.get_aliases_for_room = AsyncMock(
+            return_value=["#irc_foobar:matrix.org", "#athing:matrix.org"]
         )
-        self.store.get_local_users_in_room = simple_async_mock([])
+        self.store.get_local_users_in_room = AsyncMock(return_value=[])
         self.assertTrue(
             (
                 yield self.service.is_interested_in_event(
@@ -182,10 +181,10 @@ class ApplicationServiceTestCase(unittest.TestCase):
         self.service.namespaces[ApplicationService.NS_ALIASES].append(
             _regex("#irc_.*:matrix.org")
         )
-        self.store.get_aliases_for_room = simple_async_mock(
-            ["#xmpp_foobar:matrix.org", "#athing:matrix.org"]
+        self.store.get_aliases_for_room = AsyncMock(
+            return_value=["#xmpp_foobar:matrix.org", "#athing:matrix.org"]
         )
-        self.store.get_local_users_in_room = simple_async_mock([])
+        self.store.get_local_users_in_room = AsyncMock(return_value=[])
         self.assertFalse(
             (
                 yield defer.ensureDeferred(
@@ -205,8 +204,10 @@ class ApplicationServiceTestCase(unittest.TestCase):
         )
         self.service.namespaces[ApplicationService.NS_USERS].append(_regex("@irc_.*"))
         self.event.sender = "@irc_foobar:matrix.org"
-        self.store.get_aliases_for_room = simple_async_mock(["#irc_barfoo:matrix.org"])
-        self.store.get_local_users_in_room = simple_async_mock([])
+        self.store.get_aliases_for_room = AsyncMock(
+            return_value=["#irc_barfoo:matrix.org"]
+        )
+        self.store.get_local_users_in_room = AsyncMock(return_value=[])
         self.assertTrue(
             (
                 yield self.service.is_interested_in_event(
@@ -235,10 +236,10 @@ class ApplicationServiceTestCase(unittest.TestCase):
     def test_member_list_match(self) -> Generator["defer.Deferred[Any]", object, None]:
         self.service.namespaces[ApplicationService.NS_USERS].append(_regex("@irc_.*"))
         # Note that @irc_fo:here is the AS user.
-        self.store.get_local_users_in_room = simple_async_mock(
-            ["@alice:here", "@irc_fo:here", "@bob:here"]
+        self.store.get_local_users_in_room = AsyncMock(
+            return_value=["@alice:here", "@irc_fo:here", "@bob:here"]
         )
-        self.store.get_aliases_for_room = simple_async_mock([])
+        self.store.get_aliases_for_room = AsyncMock(return_value=[])
 
         self.event.sender = "@xmpp_foobar:matrix.org"
         self.assertTrue(
diff --git a/tests/appservice/test_scheduler.py b/tests/appservice/test_scheduler.py
index e2a3bad065..445919417e 100644
--- a/tests/appservice/test_scheduler.py
+++ b/tests/appservice/test_scheduler.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 from typing import List, Optional, Sequence, Tuple, cast
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from typing_extensions import TypeAlias
 
@@ -37,7 +37,6 @@ from synapse.types import DeviceListUpdates, JsonDict
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import simple_async_mock
 
 from ..utils import MockClock
 
@@ -62,10 +61,12 @@ class ApplicationServiceSchedulerTransactionCtrlTestCase(unittest.TestCase):
         txn = Mock(id=txn_id, service=service, events=events)
 
         # mock methods
-        self.store.get_appservice_state = simple_async_mock(ApplicationServiceState.UP)
-        txn.send = simple_async_mock(True)
-        txn.complete = simple_async_mock(True)
-        self.store.create_appservice_txn = simple_async_mock(txn)
+        self.store.get_appservice_state = AsyncMock(
+            return_value=ApplicationServiceState.UP
+        )
+        txn.send = AsyncMock(return_value=True)
+        txn.complete = AsyncMock(return_value=True)
+        self.store.create_appservice_txn = AsyncMock(return_value=txn)
 
         # actual call
         self.successResultOf(defer.ensureDeferred(self.txnctrl.send(service, events)))
@@ -89,10 +90,10 @@ class ApplicationServiceSchedulerTransactionCtrlTestCase(unittest.TestCase):
         events = [Mock(), Mock()]
 
         txn = Mock(id="idhere", service=service, events=events)
-        self.store.get_appservice_state = simple_async_mock(
-            ApplicationServiceState.DOWN
+        self.store.get_appservice_state = AsyncMock(
+            return_value=ApplicationServiceState.DOWN
         )
-        self.store.create_appservice_txn = simple_async_mock(txn)
+        self.store.create_appservice_txn = AsyncMock(return_value=txn)
 
         # actual call
         self.successResultOf(defer.ensureDeferred(self.txnctrl.send(service, events)))
@@ -118,10 +119,12 @@ class ApplicationServiceSchedulerTransactionCtrlTestCase(unittest.TestCase):
         txn = Mock(id=txn_id, service=service, events=events)
 
         # mock methods
-        self.store.get_appservice_state = simple_async_mock(ApplicationServiceState.UP)
-        self.store.set_appservice_state = simple_async_mock(True)
-        txn.send = simple_async_mock(False)  # fails to send
-        self.store.create_appservice_txn = simple_async_mock(txn)
+        self.store.get_appservice_state = AsyncMock(
+            return_value=ApplicationServiceState.UP
+        )
+        self.store.set_appservice_state = AsyncMock(return_value=True)
+        txn.send = AsyncMock(return_value=False)  # fails to send
+        self.store.create_appservice_txn = AsyncMock(return_value=txn)
 
         # actual call
         self.successResultOf(defer.ensureDeferred(self.txnctrl.send(service, events)))
@@ -150,7 +153,7 @@ class ApplicationServiceSchedulerRecovererTestCase(unittest.TestCase):
         self.as_api = Mock()
         self.store = Mock()
         self.service = Mock()
-        self.callback = simple_async_mock()
+        self.callback = AsyncMock()
         self.recoverer = _Recoverer(
             clock=cast(Clock, self.clock),
             as_api=self.as_api,
@@ -174,8 +177,8 @@ class ApplicationServiceSchedulerRecovererTestCase(unittest.TestCase):
         self.recoverer.recover()
         # shouldn't have called anything prior to waiting for exp backoff
         self.assertEqual(0, self.store.get_oldest_unsent_txn.call_count)
-        txn.send = simple_async_mock(True)
-        txn.complete = simple_async_mock(None)
+        txn.send = AsyncMock(return_value=True)
+        txn.complete = AsyncMock(return_value=None)
         # wait for exp backoff
         self.clock.advance_time(2)
         self.assertEqual(1, txn.send.call_count)
@@ -202,8 +205,8 @@ class ApplicationServiceSchedulerRecovererTestCase(unittest.TestCase):
 
         self.recoverer.recover()
         self.assertEqual(0, self.store.get_oldest_unsent_txn.call_count)
-        txn.send = simple_async_mock(False)
-        txn.complete = simple_async_mock(None)
+        txn.send = AsyncMock(return_value=False)
+        txn.complete = AsyncMock(return_value=None)
         self.clock.advance_time(2)
         self.assertEqual(1, txn.send.call_count)
         self.assertEqual(0, txn.complete.call_count)
@@ -216,7 +219,7 @@ class ApplicationServiceSchedulerRecovererTestCase(unittest.TestCase):
         self.assertEqual(3, txn.send.call_count)
         self.assertEqual(0, txn.complete.call_count)
         self.assertEqual(0, self.callback.call_count)
-        txn.send = simple_async_mock(True)  # successfully send the txn
+        txn.send = AsyncMock(return_value=True)  # successfully send the txn
         pop_txn = True  # returns the txn the first time, then no more.
         self.clock.advance_time(16)
         self.assertEqual(1, txn.send.call_count)  # new mock reset call count
@@ -244,7 +247,7 @@ class ApplicationServiceSchedulerQueuerTestCase(unittest.HomeserverTestCase):
     def prepare(self, reactor: "MemoryReactor", clock: Clock, hs: HomeServer) -> None:
         self.scheduler = ApplicationServiceScheduler(hs)
         self.txn_ctrl = Mock()
-        self.txn_ctrl.send = simple_async_mock()
+        self.txn_ctrl.send = AsyncMock()
 
         # Replace instantiated _TransactionController instances with our Mock
         self.scheduler.txn_ctrl = self.txn_ctrl
diff --git a/tests/config/test_ratelimiting.py b/tests/config/test_ratelimiting.py
index f12147eaa0..0c27dd21e2 100644
--- a/tests/config/test_ratelimiting.py
+++ b/tests/config/test_ratelimiting.py
@@ -12,11 +12,42 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 from synapse.config.homeserver import HomeServerConfig
+from synapse.config.ratelimiting import RatelimitSettings
 
 from tests.unittest import TestCase
 from tests.utils import default_config
 
 
+class ParseRatelimitSettingsTestcase(TestCase):
+    def test_depth_1(self) -> None:
+        cfg = {
+            "a": {
+                "per_second": 5,
+                "burst_count": 10,
+            }
+        }
+        parsed = RatelimitSettings.parse(cfg, "a")
+        self.assertEqual(parsed, RatelimitSettings("a", 5, 10))
+
+    def test_depth_2(self) -> None:
+        cfg = {
+            "a": {
+                "b": {
+                    "per_second": 5,
+                    "burst_count": 10,
+                },
+            }
+        }
+        parsed = RatelimitSettings.parse(cfg, "a.b")
+        self.assertEqual(parsed, RatelimitSettings("a.b", 5, 10))
+
+    def test_missing(self) -> None:
+        parsed = RatelimitSettings.parse(
+            {}, "a", defaults={"per_second": 5, "burst_count": 10}
+        )
+        self.assertEqual(parsed, RatelimitSettings("a", 5, 10))
+
+
 class RatelimitConfigTestCase(TestCase):
     def test_parse_rc_federation(self) -> None:
         config_dict = default_config("test")
diff --git a/tests/crypto/test_keyring.py b/tests/crypto/test_keyring.py
index 2be341ac7b..f93ba5d4cf 100644
--- a/tests/crypto/test_keyring.py
+++ b/tests/crypto/test_keyring.py
@@ -13,7 +13,7 @@
 # limitations under the License.
 import time
 from typing import Any, Dict, List, Optional, cast
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 import attr
 import canonicaljson
@@ -45,7 +45,6 @@ from synapse.types import JsonDict
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 from tests.unittest import logcontext_clean, override_config
 
 
@@ -291,7 +290,7 @@ class KeyringTestCase(unittest.HomeserverTestCase):
         with a null `ts_valid_until_ms`
         """
         mock_fetcher = Mock()
-        mock_fetcher.get_keys = Mock(return_value=make_awaitable({}))
+        mock_fetcher.get_keys = AsyncMock(return_value={})
 
         key1 = signedjson.key.generate_signing_key("1")
         r = self.hs.get_datastores().main.store_server_signature_keys(
diff --git a/tests/events/test_presence_router.py b/tests/events/test_presence_router.py
index 6fb1f1bd6e..0fcfe38efa 100644
--- a/tests/events/test_presence_router.py
+++ b/tests/events/test_presence_router.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 from typing import Dict, Iterable, List, Optional, Set, Tuple, Union
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 import attr
 
@@ -30,7 +30,6 @@ from synapse.types import JsonDict, StreamToken, create_requester
 from synapse.util import Clock
 
 from tests.handlers.test_sync import generate_sync_config
-from tests.test_utils import simple_async_mock
 from tests.unittest import (
     FederatingHomeserverTestCase,
     HomeserverTestCase,
@@ -157,7 +156,7 @@ class PresenceRouterTestCase(FederatingHomeserverTestCase):
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
         # Mock out the calls over federation.
         self.fed_transport_client = Mock(spec=["send_transaction"])
-        self.fed_transport_client.send_transaction = simple_async_mock({})
+        self.fed_transport_client.send_transaction = AsyncMock(return_value={})
 
         hs = self.setup_test_homeserver(
             federation_transport_client=self.fed_transport_client,
diff --git a/tests/federation/test_complexity.py b/tests/federation/test_complexity.py
index 129d7cfd93..73a2766baf 100644
--- a/tests/federation/test_complexity.py
+++ b/tests/federation/test_complexity.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
-from unittest.mock import Mock
+from unittest.mock import AsyncMock
 
 from synapse.api.errors import Codes, SynapseError
 from synapse.rest import admin
@@ -20,7 +20,6 @@ from synapse.rest.client import login, room
 from synapse.types import JsonDict, UserID, create_requester
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 
 
 class RoomComplexityTests(unittest.FederatingHomeserverTestCase):
@@ -58,7 +57,7 @@ class RoomComplexityTests(unittest.FederatingHomeserverTestCase):
         async def get_current_state_event_counts(room_id: str) -> int:
             return int(500 * 1.23)
 
-        store.get_current_state_event_counts = get_current_state_event_counts  # type: ignore[assignment]
+        store.get_current_state_event_counts = get_current_state_event_counts  # type: ignore[method-assign]
 
         # Get the room complexity again -- make sure it's our artificial value
         channel = self.make_signed_federation_request(
@@ -75,9 +74,9 @@ class RoomComplexityTests(unittest.FederatingHomeserverTestCase):
         fed_transport = self.hs.get_federation_transport_client()
 
         # Mock out some things, because we don't want to test the whole join
-        fed_transport.client.get_json = Mock(return_value=make_awaitable({"v1": 9999}))  # type: ignore[assignment]
-        handler.federation_handler.do_invite_join = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(("", 1))
+        fed_transport.client.get_json = AsyncMock(return_value={"v1": 9999})  # type: ignore[method-assign]
+        handler.federation_handler.do_invite_join = AsyncMock(  # type: ignore[method-assign]
+            return_value=("", 1)
         )
 
         d = handler._remote_join(
@@ -106,9 +105,9 @@ class RoomComplexityTests(unittest.FederatingHomeserverTestCase):
         fed_transport = self.hs.get_federation_transport_client()
 
         # Mock out some things, because we don't want to test the whole join
-        fed_transport.client.get_json = Mock(return_value=make_awaitable({"v1": 9999}))  # type: ignore[assignment]
-        handler.federation_handler.do_invite_join = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(("", 1))
+        fed_transport.client.get_json = AsyncMock(return_value={"v1": 9999})  # type: ignore[method-assign]
+        handler.federation_handler.do_invite_join = AsyncMock(  # type: ignore[method-assign]
+            return_value=("", 1)
         )
 
         d = handler._remote_join(
@@ -143,16 +142,16 @@ class RoomComplexityTests(unittest.FederatingHomeserverTestCase):
         fed_transport = self.hs.get_federation_transport_client()
 
         # Mock out some things, because we don't want to test the whole join
-        fed_transport.client.get_json = Mock(return_value=make_awaitable(None))  # type: ignore[assignment]
-        handler.federation_handler.do_invite_join = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(("", 1))
+        fed_transport.client.get_json = AsyncMock(return_value=None)  # type: ignore[method-assign]
+        handler.federation_handler.do_invite_join = AsyncMock(  # type: ignore[method-assign]
+            return_value=("", 1)
         )
 
         # Artificially raise the complexity
         async def get_current_state_event_counts(room_id: str) -> int:
             return 600
 
-        self.hs.get_datastores().main.get_current_state_event_counts = get_current_state_event_counts  # type: ignore[assignment]
+        self.hs.get_datastores().main.get_current_state_event_counts = get_current_state_event_counts  # type: ignore[method-assign]
 
         d = handler._remote_join(
             create_requester(u1),
@@ -200,9 +199,9 @@ class RoomComplexityAdminTests(unittest.FederatingHomeserverTestCase):
         fed_transport = self.hs.get_federation_transport_client()
 
         # Mock out some things, because we don't want to test the whole join
-        fed_transport.client.get_json = Mock(return_value=make_awaitable({"v1": 9999}))  # type: ignore[assignment]
-        handler.federation_handler.do_invite_join = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(("", 1))
+        fed_transport.client.get_json = AsyncMock(return_value={"v1": 9999})  # type: ignore[method-assign]
+        handler.federation_handler.do_invite_join = AsyncMock(  # type: ignore[method-assign]
+            return_value=("", 1)
         )
 
         d = handler._remote_join(
@@ -230,9 +229,9 @@ class RoomComplexityAdminTests(unittest.FederatingHomeserverTestCase):
         fed_transport = self.hs.get_federation_transport_client()
 
         # Mock out some things, because we don't want to test the whole join
-        fed_transport.client.get_json = Mock(return_value=make_awaitable({"v1": 9999}))  # type: ignore[assignment]
-        handler.federation_handler.do_invite_join = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(("", 1))
+        fed_transport.client.get_json = AsyncMock(return_value={"v1": 9999})  # type: ignore[method-assign]
+        handler.federation_handler.do_invite_join = AsyncMock(  # type: ignore[method-assign]
+            return_value=("", 1)
         )
 
         d = handler._remote_join(
diff --git a/tests/federation/test_federation_catch_up.py b/tests/federation/test_federation_catch_up.py
index b290b020a2..75ae740b43 100644
--- a/tests/federation/test_federation_catch_up.py
+++ b/tests/federation/test_federation_catch_up.py
@@ -1,6 +1,6 @@
 from typing import Callable, Collection, List, Optional, Tuple
 from unittest import mock
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -19,7 +19,7 @@ from synapse.types import JsonDict
 from synapse.util import Clock
 from synapse.util.retryutils import NotRetryingDestination
 
-from tests.test_utils import event_injection, make_awaitable
+from tests.test_utils import event_injection
 from tests.unittest import FederatingHomeserverTestCase
 
 
@@ -50,8 +50,8 @@ class FederationCatchUpTestCases(FederatingHomeserverTestCase):
         # This mock is crucial for destination_rooms to be populated.
         # TODO: this seems to no longer be the case---tests pass with this mock
         # commented out.
-        state_storage_controller.get_current_hosts_in_room = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable({"test", "host2"})
+        state_storage_controller.get_current_hosts_in_room = AsyncMock(  # type: ignore[method-assign]
+            return_value={"test", "host2"}
         )
 
         # whenever send_transaction is called, record the pdu data
@@ -436,7 +436,7 @@ class FederationCatchUpTestCases(FederatingHomeserverTestCase):
         def wake_destination_track(destination: str) -> None:
             woken.add(destination)
 
-        self.federation_sender.wake_destination = wake_destination_track  # type: ignore[assignment]
+        self.federation_sender.wake_destination = wake_destination_track  # type: ignore[method-assign]
 
         # We wait quite long so that all dests can be woken up, since there is a delay
         # between them.
diff --git a/tests/federation/test_federation_sender.py b/tests/federation/test_federation_sender.py
index 9e104fd96a..caf04b54cb 100644
--- a/tests/federation/test_federation_sender.py
+++ b/tests/federation/test_federation_sender.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 from typing import Callable, FrozenSet, List, Optional, Set
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from signedjson import key, sign
 from signedjson.types import BaseKey, SigningKey
@@ -29,7 +29,6 @@ from synapse.server import HomeServer
 from synapse.types import JsonDict, ReadReceipt
 from synapse.util import Clock
 
-from tests.test_utils import make_awaitable
 from tests.unittest import HomeserverTestCase
 
 
@@ -43,15 +42,16 @@ class FederationSenderReceiptsTestCases(HomeserverTestCase):
 
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
         self.federation_transport_client = Mock(spec=["send_transaction"])
+        self.federation_transport_client.send_transaction = AsyncMock()
         hs = self.setup_test_homeserver(
             federation_transport_client=self.federation_transport_client,
         )
 
-        hs.get_storage_controllers().state.get_current_hosts_in_room = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable({"test", "host2"})
+        hs.get_storage_controllers().state.get_current_hosts_in_room = AsyncMock(  # type: ignore[method-assign]
+            return_value={"test", "host2"}
         )
 
-        hs.get_storage_controllers().state.get_current_hosts_in_room_or_partial_state_approximation = (  # type: ignore[assignment]
+        hs.get_storage_controllers().state.get_current_hosts_in_room_or_partial_state_approximation = (  # type: ignore[method-assign]
             hs.get_storage_controllers().state.get_current_hosts_in_room
         )
 
@@ -64,7 +64,7 @@ class FederationSenderReceiptsTestCases(HomeserverTestCase):
 
     def test_send_receipts(self) -> None:
         mock_send_transaction = self.federation_transport_client.send_transaction
-        mock_send_transaction.return_value = make_awaitable({})
+        mock_send_transaction.return_value = {}
 
         sender = self.hs.get_federation_sender()
         receipt = ReadReceipt(
@@ -75,7 +75,7 @@ class FederationSenderReceiptsTestCases(HomeserverTestCase):
             thread_id=None,
             data={"ts": 1234},
         )
-        self.successResultOf(defer.ensureDeferred(sender.send_read_receipt(receipt)))
+        self.get_success(sender.send_read_receipt(receipt))
 
         self.pump()
 
@@ -104,13 +104,16 @@ class FederationSenderReceiptsTestCases(HomeserverTestCase):
 
     def test_send_receipts_thread(self) -> None:
         mock_send_transaction = self.federation_transport_client.send_transaction
-        mock_send_transaction.return_value = make_awaitable({})
+        mock_send_transaction.return_value = {}
 
         # Create receipts for:
         #
         # * The same room / user on multiple threads.
         # * A different user in the same room.
         sender = self.hs.get_federation_sender()
+        # Hack so that we have a txn in-flight so we batch up read receipts
+        # below
+        sender.wake_destination("host2")
         for user, thread in (
             ("alice", None),
             ("alice", "thread"),
@@ -125,9 +128,7 @@ class FederationSenderReceiptsTestCases(HomeserverTestCase):
                 thread_id=thread,
                 data={"ts": 1234},
             )
-            self.successResultOf(
-                defer.ensureDeferred(sender.send_read_receipt(receipt))
-            )
+            defer.ensureDeferred(sender.send_read_receipt(receipt))
 
         self.pump()
 
@@ -180,7 +181,7 @@ class FederationSenderReceiptsTestCases(HomeserverTestCase):
         """Send two receipts in quick succession; the second should be flushed, but
         only after 20ms"""
         mock_send_transaction = self.federation_transport_client.send_transaction
-        mock_send_transaction.return_value = make_awaitable({})
+        mock_send_transaction.return_value = {}
 
         sender = self.hs.get_federation_sender()
         receipt = ReadReceipt(
@@ -191,7 +192,7 @@ class FederationSenderReceiptsTestCases(HomeserverTestCase):
             thread_id=None,
             data={"ts": 1234},
         )
-        self.successResultOf(defer.ensureDeferred(sender.send_read_receipt(receipt)))
+        self.get_success(sender.send_read_receipt(receipt))
 
         self.pump()
 
@@ -276,6 +277,8 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
         self.federation_transport_client = Mock(
             spec=["send_transaction", "query_user_devices"]
         )
+        self.federation_transport_client.send_transaction = AsyncMock()
+        self.federation_transport_client.query_user_devices = AsyncMock()
         return self.setup_test_homeserver(
             federation_transport_client=self.federation_transport_client,
         )
@@ -317,13 +320,13 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
             self.record_transaction
         )
 
-    def record_transaction(
+    async def record_transaction(
         self, txn: Transaction, json_cb: Optional[Callable[[], JsonDict]] = None
-    ) -> "defer.Deferred[JsonDict]":
+    ) -> JsonDict:
         assert json_cb is not None
         data = json_cb()
         self.edus.extend(data["edus"])
-        return defer.succeed({})
+        return {}
 
     def test_send_device_updates(self) -> None:
         """Basic case: each device update should result in an EDU"""
@@ -340,7 +343,9 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
         self.reactor.advance(1)
 
         # a second call should produce no new device EDUs
-        self.hs.get_federation_sender().send_device_messages("host2")
+        self.get_success(
+            self.hs.get_federation_sender().send_device_messages(["host2"])
+        )
         self.assertEqual(self.edus, [])
 
         # a second device
@@ -354,15 +359,11 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
 
         # Send the server a device list EDU for the other user, this will cause
         # it to try and resync the device lists.
-        self.federation_transport_client.query_user_devices.return_value = (
-            make_awaitable(
-                {
-                    "stream_id": "1",
-                    "user_id": "@user2:host2",
-                    "devices": [{"device_id": "D1"}],
-                }
-            )
-        )
+        self.federation_transport_client.query_user_devices.return_value = {
+            "stream_id": "1",
+            "user_id": "@user2:host2",
+            "devices": [{"device_id": "D1"}],
+        }
 
         self.get_success(
             self.device_handler.device_list_updater.incoming_device_list_update(
@@ -533,7 +534,7 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
         recovery
         """
         mock_send_txn = self.federation_transport_client.send_transaction
-        mock_send_txn.side_effect = lambda t, cb: defer.fail(AssertionError("fail"))
+        mock_send_txn.side_effect = AssertionError("fail")
 
         # create devices
         u1 = self.register_user("user", "pass")
@@ -552,7 +553,9 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
 
         # recover the server
         mock_send_txn.side_effect = self.record_transaction
-        self.hs.get_federation_sender().send_device_messages("host2")
+        self.get_success(
+            self.hs.get_federation_sender().send_device_messages(["host2"])
+        )
 
         # We queue up device list updates to be sent over federation, so we
         # advance to clear the queue.
@@ -578,7 +581,7 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
         This case tests the behaviour when the server has never been reachable.
         """
         mock_send_txn = self.federation_transport_client.send_transaction
-        mock_send_txn.side_effect = lambda t, cb: defer.fail(AssertionError("fail"))
+        mock_send_txn.side_effect = AssertionError("fail")
 
         # create devices
         u1 = self.register_user("user", "pass")
@@ -603,7 +606,9 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
 
         # recover the server
         mock_send_txn.side_effect = self.record_transaction
-        self.hs.get_federation_sender().send_device_messages("host2")
+        self.get_success(
+            self.hs.get_federation_sender().send_device_messages(["host2"])
+        )
 
         # We queue up device list updates to be sent over federation, so we
         # advance to clear the queue.
@@ -636,7 +641,7 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
 
         # now the server goes offline
         mock_send_txn = self.federation_transport_client.send_transaction
-        mock_send_txn.side_effect = lambda t, cb: defer.fail(AssertionError("fail"))
+        mock_send_txn.side_effect = AssertionError("fail")
 
         self.login("user", "pass", device_id="D2")
         self.login("user", "pass", device_id="D3")
@@ -658,7 +663,9 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
 
         # recover the server
         mock_send_txn.side_effect = self.record_transaction
-        self.hs.get_federation_sender().send_device_messages("host2")
+        self.get_success(
+            self.hs.get_federation_sender().send_device_messages(["host2"])
+        )
 
         # We queue up device list updates to be sent over federation, so we
         # advance to clear the queue.
diff --git a/tests/federation/transport/test_knocking.py b/tests/federation/transport/test_knocking.py
index 70209ab090..3f42f79f26 100644
--- a/tests/federation/transport/test_knocking.py
+++ b/tests/federation/transport/test_knocking.py
@@ -218,7 +218,7 @@ class FederationKnockingTestCase(
         ) -> EventBase:
             return pdu
 
-        homeserver.get_federation_server()._check_sigs_and_hash = (  # type: ignore[assignment]
+        homeserver.get_federation_server()._check_sigs_and_hash = (  # type: ignore[method-assign]
             approve_all_signature_checking
         )
 
@@ -229,7 +229,7 @@ class FederationKnockingTestCase(
         ) -> None:
             pass
 
-        homeserver.get_federation_event_handler()._check_event_auth = _check_event_auth  # type: ignore[assignment]
+        homeserver.get_federation_event_handler()._check_event_auth = _check_event_auth  # type: ignore[method-assign]
 
         return super().prepare(reactor, clock, homeserver)
 
diff --git a/tests/handlers/test_appservice.py b/tests/handlers/test_appservice.py
index 9014e60577..46d022092e 100644
--- a/tests/handlers/test_appservice.py
+++ b/tests/handlers/test_appservice.py
@@ -13,7 +13,7 @@
 # limitations under the License.
 
 from typing import Dict, Iterable, List, Optional
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from parameterized import parameterized
 
@@ -36,7 +36,7 @@ from synapse.util import Clock
 from synapse.util.stringutils import random_string
 
 from tests import unittest
-from tests.test_utils import event_injection, make_awaitable, simple_async_mock
+from tests.test_utils import event_injection
 from tests.unittest import override_config
 from tests.utils import MockClock
 
@@ -46,15 +46,13 @@ class AppServiceHandlerTestCase(unittest.TestCase):
 
     def setUp(self) -> None:
         self.mock_store = Mock()
-        self.mock_as_api = Mock()
+        self.mock_as_api = AsyncMock()
         self.mock_scheduler = Mock()
         hs = Mock()
         hs.get_datastores.return_value = Mock(main=self.mock_store)
-        self.mock_store.get_appservice_last_pos.return_value = make_awaitable(None)
-        self.mock_store.set_appservice_last_pos.return_value = make_awaitable(None)
-        self.mock_store.set_appservice_stream_type_pos.return_value = make_awaitable(
-            None
-        )
+        self.mock_store.get_appservice_last_pos = AsyncMock(return_value=None)
+        self.mock_store.set_appservice_last_pos = AsyncMock(return_value=None)
+        self.mock_store.set_appservice_stream_type_pos = AsyncMock(return_value=None)
         hs.get_application_service_api.return_value = self.mock_as_api
         hs.get_application_service_scheduler.return_value = self.mock_scheduler
         hs.get_clock.return_value = MockClock()
@@ -69,21 +67,25 @@ class AppServiceHandlerTestCase(unittest.TestCase):
             self._mkservice(is_interested_in_event=False),
         ]
 
-        self.mock_as_api.query_user.return_value = make_awaitable(True)
+        self.mock_as_api.query_user.return_value = True
         self.mock_store.get_app_services.return_value = services
-        self.mock_store.get_user_by_id.return_value = make_awaitable([])
+        self.mock_store.get_user_by_id = AsyncMock(return_value=[])
 
         event = Mock(
             sender="@someone:anywhere", type="m.room.message", room_id="!foo:bar"
         )
-        self.mock_store.get_all_new_event_ids_stream.side_effect = [
-            make_awaitable((0, {})),
-            make_awaitable((1, {event.event_id: 0})),
-        ]
-        self.mock_store.get_events_as_list.side_effect = [
-            make_awaitable([]),
-            make_awaitable([event]),
-        ]
+        self.mock_store.get_all_new_event_ids_stream = AsyncMock(
+            side_effect=[
+                (0, {}),
+                (1, {event.event_id: 0}),
+            ]
+        )
+        self.mock_store.get_events_as_list = AsyncMock(
+            side_effect=[
+                [],
+                [event],
+            ]
+        )
         self.handler.notify_interested_services(RoomStreamToken(None, 1))
 
         self.mock_scheduler.enqueue_for_appservice.assert_called_once_with(
@@ -95,14 +97,16 @@ class AppServiceHandlerTestCase(unittest.TestCase):
         services = [self._mkservice(is_interested_in_event=True)]
         services[0].is_interested_in_user.return_value = True
         self.mock_store.get_app_services.return_value = services
-        self.mock_store.get_user_by_id.return_value = make_awaitable(None)
+        self.mock_store.get_user_by_id = AsyncMock(return_value=None)
 
         event = Mock(sender=user_id, type="m.room.message", room_id="!foo:bar")
-        self.mock_as_api.query_user.return_value = make_awaitable(True)
-        self.mock_store.get_all_new_event_ids_stream.side_effect = [
-            make_awaitable((0, {event.event_id: 0})),
-        ]
-        self.mock_store.get_events_as_list.side_effect = [make_awaitable([event])]
+        self.mock_as_api.query_user.return_value = True
+        self.mock_store.get_all_new_event_ids_stream = AsyncMock(
+            side_effect=[
+                (0, {event.event_id: 0}),
+            ]
+        )
+        self.mock_store.get_events_as_list = AsyncMock(side_effect=[[event]])
         self.handler.notify_interested_services(RoomStreamToken(None, 0))
 
         self.mock_as_api.query_user.assert_called_once_with(services[0], user_id)
@@ -112,13 +116,15 @@ class AppServiceHandlerTestCase(unittest.TestCase):
         services = [self._mkservice(is_interested_in_event=True)]
         services[0].is_interested_in_user.return_value = True
         self.mock_store.get_app_services.return_value = services
-        self.mock_store.get_user_by_id.return_value = make_awaitable({"name": user_id})
+        self.mock_store.get_user_by_id = AsyncMock(return_value={"name": user_id})
 
         event = Mock(sender=user_id, type="m.room.message", room_id="!foo:bar")
-        self.mock_as_api.query_user.return_value = make_awaitable(True)
-        self.mock_store.get_all_new_event_ids_stream.side_effect = [
-            make_awaitable((0, [event], {event.event_id: 0})),
-        ]
+        self.mock_as_api.query_user.return_value = True
+        self.mock_store.get_all_new_event_ids_stream = AsyncMock(
+            side_effect=[
+                (0, [event], {event.event_id: 0}),
+            ]
+        )
 
         self.handler.notify_interested_services(RoomStreamToken(None, 0))
 
@@ -141,10 +147,10 @@ class AppServiceHandlerTestCase(unittest.TestCase):
             self._mkservice_alias(is_room_alias_in_namespace=False),
         ]
 
-        self.mock_as_api.query_alias.return_value = make_awaitable(True)
+        self.mock_as_api.query_alias = AsyncMock(return_value=True)
         self.mock_store.get_app_services.return_value = services
-        self.mock_store.get_association_from_room_alias.return_value = make_awaitable(
-            Mock(room_id=room_id, servers=servers)
+        self.mock_store.get_association_from_room_alias = AsyncMock(
+            return_value=Mock(room_id=room_id, servers=servers)
         )
 
         result = self.successResultOf(
@@ -177,7 +183,7 @@ class AppServiceHandlerTestCase(unittest.TestCase):
     def test_get_3pe_protocols_protocol_no_response(self) -> None:
         service = self._mkservice(False, ["my-protocol"])
         self.mock_store.get_app_services.return_value = [service]
-        self.mock_as_api.get_3pe_protocol.return_value = make_awaitable(None)
+        self.mock_as_api.get_3pe_protocol.return_value = None
         response = self.successResultOf(
             defer.ensureDeferred(self.handler.get_3pe_protocols())
         )
@@ -189,9 +195,10 @@ class AppServiceHandlerTestCase(unittest.TestCase):
     def test_get_3pe_protocols_select_one_protocol(self) -> None:
         service = self._mkservice(False, ["my-protocol"])
         self.mock_store.get_app_services.return_value = [service]
-        self.mock_as_api.get_3pe_protocol.return_value = make_awaitable(
-            {"x-protocol-data": 42, "instances": []}
-        )
+        self.mock_as_api.get_3pe_protocol.return_value = {
+            "x-protocol-data": 42,
+            "instances": [],
+        }
         response = self.successResultOf(
             defer.ensureDeferred(self.handler.get_3pe_protocols("my-protocol"))
         )
@@ -205,9 +212,10 @@ class AppServiceHandlerTestCase(unittest.TestCase):
     def test_get_3pe_protocols_one_protocol(self) -> None:
         service = self._mkservice(False, ["my-protocol"])
         self.mock_store.get_app_services.return_value = [service]
-        self.mock_as_api.get_3pe_protocol.return_value = make_awaitable(
-            {"x-protocol-data": 42, "instances": []}
-        )
+        self.mock_as_api.get_3pe_protocol.return_value = {
+            "x-protocol-data": 42,
+            "instances": [],
+        }
         response = self.successResultOf(
             defer.ensureDeferred(self.handler.get_3pe_protocols())
         )
@@ -222,9 +230,10 @@ class AppServiceHandlerTestCase(unittest.TestCase):
         service_one = self._mkservice(False, ["my-protocol"])
         service_two = self._mkservice(False, ["other-protocol"])
         self.mock_store.get_app_services.return_value = [service_one, service_two]
-        self.mock_as_api.get_3pe_protocol.return_value = make_awaitable(
-            {"x-protocol-data": 42, "instances": []}
-        )
+        self.mock_as_api.get_3pe_protocol.return_value = {
+            "x-protocol-data": 42,
+            "instances": [],
+        }
         response = self.successResultOf(
             defer.ensureDeferred(self.handler.get_3pe_protocols())
         )
@@ -287,13 +296,11 @@ class AppServiceHandlerTestCase(unittest.TestCase):
         interested_service = self._mkservice(is_interested_in_event=True)
         services = [interested_service]
         self.mock_store.get_app_services.return_value = services
-        self.mock_store.get_type_stream_id_for_appservice.return_value = make_awaitable(
-            579
-        )
+        self.mock_store.get_type_stream_id_for_appservice = AsyncMock(return_value=579)
 
         event = Mock(event_id="event_1")
-        self.event_source.sources.receipt.get_new_events_as.return_value = (
-            make_awaitable(([event], None))
+        self.event_source.sources.receipt.get_new_events_as = AsyncMock(
+            return_value=([event], None)
         )
 
         self.handler.notify_interested_services_ephemeral(
@@ -317,13 +324,11 @@ class AppServiceHandlerTestCase(unittest.TestCase):
         services = [interested_service]
 
         self.mock_store.get_app_services.return_value = services
-        self.mock_store.get_type_stream_id_for_appservice.return_value = make_awaitable(
-            580
-        )
+        self.mock_store.get_type_stream_id_for_appservice = AsyncMock(return_value=580)
 
         event = Mock(event_id="event_1")
-        self.event_source.sources.receipt.get_new_events_as.return_value = (
-            make_awaitable(([event], None))
+        self.event_source.sources.receipt.get_new_events_as = AsyncMock(
+            return_value=([event], None)
         )
 
         self.handler.notify_interested_services_ephemeral(
@@ -350,9 +355,7 @@ class AppServiceHandlerTestCase(unittest.TestCase):
             A mock representing the ApplicationService.
         """
         service = Mock()
-        service.is_interested_in_event.return_value = make_awaitable(
-            is_interested_in_event
-        )
+        service.is_interested_in_event = AsyncMock(return_value=is_interested_in_event)
         service.token = "mock_service_token"
         service.url = "mock_service_url"
         service.protocols = protocols
@@ -396,12 +399,12 @@ class ApplicationServicesHandlerSendEventsTestCase(unittest.HomeserverTestCase):
         self.hs = hs
         # Mock the ApplicationServiceScheduler's _TransactionController's send method so that
         # we can track any outgoing ephemeral events
-        self.send_mock = simple_async_mock()
-        hs.get_application_service_handler().scheduler.txn_ctrl.send = self.send_mock  # type: ignore[assignment]
+        self.send_mock = AsyncMock()
+        hs.get_application_service_handler().scheduler.txn_ctrl.send = self.send_mock  # type: ignore[method-assign]
 
         # Mock out application services, and allow defining our own in tests
         self._services: List[ApplicationService] = []
-        self.hs.get_datastores().main.get_app_services = Mock(  # type: ignore[assignment]
+        self.hs.get_datastores().main.get_app_services = Mock(  # type: ignore[method-assign]
             return_value=self._services
         )
 
@@ -894,12 +897,12 @@ class ApplicationServicesHandlerDeviceListsTestCase(unittest.HomeserverTestCase)
 
         # Mock ApplicationServiceApi's put_json, so we can verify the raw JSON that
         # will be sent over the wire
-        self.put_json = simple_async_mock()
-        hs.get_application_service_api().put_json = self.put_json  # type: ignore[assignment]
+        self.put_json = AsyncMock()
+        hs.get_application_service_api().put_json = self.put_json  # type: ignore[method-assign]
 
         # Mock out application services, and allow defining our own in tests
         self._services: List[ApplicationService] = []
-        self.hs.get_datastores().main.get_app_services = Mock(  # type: ignore[assignment]
+        self.hs.get_datastores().main.get_app_services = Mock(  # type: ignore[method-assign]
             return_value=self._services
         )
 
@@ -1000,8 +1003,8 @@ class ApplicationServicesHandlerOtkCountsTestCase(unittest.HomeserverTestCase):
     def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
         # Mock the ApplicationServiceScheduler's _TransactionController's send method so that
         # we can track what's going out
-        self.send_mock = simple_async_mock()
-        hs.get_application_service_handler().scheduler.txn_ctrl.send = self.send_mock  # type: ignore[assignment]  # We assign to a method.
+        self.send_mock = AsyncMock()
+        hs.get_application_service_handler().scheduler.txn_ctrl.send = self.send_mock  # type: ignore[method-assign]  # We assign to a method.
 
         # Define an application service for the tests
         self._service_token = "VERYSECRET"
diff --git a/tests/handlers/test_auth.py b/tests/handlers/test_auth.py
index 036dbbc45b..413ff8795b 100644
--- a/tests/handlers/test_auth.py
+++ b/tests/handlers/test_auth.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 from typing import Optional
-from unittest.mock import Mock
+from unittest.mock import AsyncMock
 
 import pymacaroons
 
@@ -25,7 +25,6 @@ from synapse.server import HomeServer
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 
 
 class AuthTestCase(unittest.HomeserverTestCase):
@@ -166,8 +165,8 @@ class AuthTestCase(unittest.HomeserverTestCase):
 
     def test_mau_limits_exceeded_large(self) -> None:
         self.auth_blocking._limit_usage_by_mau = True
-        self.hs.get_datastores().main.get_monthly_active_count = Mock(
-            return_value=make_awaitable(self.large_number_of_users)
+        self.hs.get_datastores().main.get_monthly_active_count = AsyncMock(
+            return_value=self.large_number_of_users
         )
 
         self.get_failure(
@@ -177,8 +176,8 @@ class AuthTestCase(unittest.HomeserverTestCase):
             ResourceLimitError,
         )
 
-        self.hs.get_datastores().main.get_monthly_active_count = Mock(
-            return_value=make_awaitable(self.large_number_of_users)
+        self.hs.get_datastores().main.get_monthly_active_count = AsyncMock(
+            return_value=self.large_number_of_users
         )
         token = self.get_success(
             self.auth_handler.create_login_token_for_user_id(self.user1)
@@ -191,8 +190,8 @@ class AuthTestCase(unittest.HomeserverTestCase):
         self.auth_blocking._limit_usage_by_mau = True
 
         # Set the server to be at the edge of too many users.
-        self.hs.get_datastores().main.get_monthly_active_count = Mock(
-            return_value=make_awaitable(self.auth_blocking._max_mau_value)
+        self.hs.get_datastores().main.get_monthly_active_count = AsyncMock(
+            return_value=self.auth_blocking._max_mau_value
         )
 
         # If not in monthly active cohort
@@ -208,8 +207,8 @@ class AuthTestCase(unittest.HomeserverTestCase):
         self.assertIsNone(self.token_login(token))
 
         # If in monthly active cohort
-        self.hs.get_datastores().main.user_last_seen_monthly_active = Mock(
-            return_value=make_awaitable(self.clock.time_msec())
+        self.hs.get_datastores().main.user_last_seen_monthly_active = AsyncMock(
+            return_value=self.clock.time_msec()
         )
         self.get_success(
             self.auth_handler.create_access_token_for_user_id(
@@ -224,8 +223,8 @@ class AuthTestCase(unittest.HomeserverTestCase):
     def test_mau_limits_not_exceeded(self) -> None:
         self.auth_blocking._limit_usage_by_mau = True
 
-        self.hs.get_datastores().main.get_monthly_active_count = Mock(
-            return_value=make_awaitable(self.small_number_of_users)
+        self.hs.get_datastores().main.get_monthly_active_count = AsyncMock(
+            return_value=self.small_number_of_users
         )
         # Ensure does not raise exception
         self.get_success(
@@ -234,8 +233,8 @@ class AuthTestCase(unittest.HomeserverTestCase):
             )
         )
 
-        self.hs.get_datastores().main.get_monthly_active_count = Mock(
-            return_value=make_awaitable(self.small_number_of_users)
+        self.hs.get_datastores().main.get_monthly_active_count = AsyncMock(
+            return_value=self.small_number_of_users
         )
         token = self.get_success(
             self.auth_handler.create_login_token_for_user_id(self.user1)
diff --git a/tests/handlers/test_cas.py b/tests/handlers/test_cas.py
index 63aad0d10c..8582b1cd1e 100644
--- a/tests/handlers/test_cas.py
+++ b/tests/handlers/test_cas.py
@@ -12,7 +12,7 @@
 #  See the License for the specific language governing permissions and
 #  limitations under the License.
 from typing import Any, Dict
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -20,7 +20,6 @@ from synapse.handlers.cas import CasResponse
 from synapse.server import HomeServer
 from synapse.util import Clock
 
-from tests.test_utils import simple_async_mock
 from tests.unittest import HomeserverTestCase, override_config
 
 # These are a few constants that are used as config parameters in the tests.
@@ -61,7 +60,7 @@ class CasHandlerTestCase(HomeserverTestCase):
 
         # stub out the auth handler
         auth_handler = self.hs.get_auth_handler()
-        auth_handler.complete_sso_login = simple_async_mock()  # type: ignore[assignment]
+        auth_handler.complete_sso_login = AsyncMock()  # type: ignore[method-assign]
 
         cas_response = CasResponse("test_user", {})
         request = _mock_request()
@@ -89,7 +88,7 @@ class CasHandlerTestCase(HomeserverTestCase):
 
         # stub out the auth handler
         auth_handler = self.hs.get_auth_handler()
-        auth_handler.complete_sso_login = simple_async_mock()  # type: ignore[assignment]
+        auth_handler.complete_sso_login = AsyncMock()  # type: ignore[method-assign]
 
         # Map a user via SSO.
         cas_response = CasResponse("test_user", {})
@@ -129,7 +128,7 @@ class CasHandlerTestCase(HomeserverTestCase):
 
         # stub out the auth handler
         auth_handler = self.hs.get_auth_handler()
-        auth_handler.complete_sso_login = simple_async_mock()  # type: ignore[assignment]
+        auth_handler.complete_sso_login = AsyncMock()  # type: ignore[method-assign]
 
         cas_response = CasResponse("föö", {})
         request = _mock_request()
@@ -160,7 +159,7 @@ class CasHandlerTestCase(HomeserverTestCase):
 
         # stub out the auth handler
         auth_handler = self.hs.get_auth_handler()
-        auth_handler.complete_sso_login = simple_async_mock()  # type: ignore[assignment]
+        auth_handler.complete_sso_login = AsyncMock()  # type: ignore[method-assign]
 
         # The response doesn't have the proper userGroup or department.
         cas_response = CasResponse("test_user", {})
diff --git a/tests/handlers/test_device.py b/tests/handlers/test_device.py
index e1e58fa6e6..55a4f95ef3 100644
--- a/tests/handlers/test_device.py
+++ b/tests/handlers/test_device.py
@@ -32,7 +32,6 @@ from synapse.types import JsonDict, create_requester
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 from tests.unittest import override_config
 
 user1 = "@boris:aaa"
@@ -41,7 +40,7 @@ user2 = "@theresa:bbb"
 
 class DeviceTestCase(unittest.HomeserverTestCase):
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
-        self.appservice_api = mock.Mock()
+        self.appservice_api = mock.AsyncMock()
         hs = self.setup_test_homeserver(
             "server",
             application_service_api=self.appservice_api,
@@ -123,50 +122,50 @@ class DeviceTestCase(unittest.HomeserverTestCase):
 
         self.assertEqual(3, len(res))
         device_map = {d["device_id"]: d for d in res}
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "user_id": user1,
                 "device_id": "xyz",
                 "display_name": "display 0",
                 "last_seen_ip": None,
                 "last_seen_ts": None,
-            },
-            device_map["xyz"],
+            }.items(),
+            device_map["xyz"].items(),
         )
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "user_id": user1,
                 "device_id": "fco",
                 "display_name": "display 1",
                 "last_seen_ip": "ip1",
                 "last_seen_ts": 1000000,
-            },
-            device_map["fco"],
+            }.items(),
+            device_map["fco"].items(),
         )
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "user_id": user1,
                 "device_id": "abc",
                 "display_name": "display 2",
                 "last_seen_ip": "ip3",
                 "last_seen_ts": 3000000,
-            },
-            device_map["abc"],
+            }.items(),
+            device_map["abc"].items(),
         )
 
     def test_get_device(self) -> None:
         self._record_users()
 
         res = self.get_success(self.handler.get_device(user1, "abc"))
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "user_id": user1,
                 "device_id": "abc",
                 "display_name": "display 2",
                 "last_seen_ip": "ip3",
                 "last_seen_ts": 3000000,
-            },
-            res,
+            }.items(),
+            res.items(),
         )
 
     def test_delete_device(self) -> None:
@@ -375,13 +374,11 @@ class DeviceTestCase(unittest.HomeserverTestCase):
         )
 
         # Setup a response.
-        self.appservice_api.query_keys.return_value = make_awaitable(
-            {
-                "device_keys": {
-                    local_user: {device_2: device_key_2b, device_3: device_key_3}
-                }
+        self.appservice_api.query_keys.return_value = {
+            "device_keys": {
+                local_user: {device_2: device_key_2b, device_3: device_key_3}
             }
-        )
+        }
 
         # Request all devices.
         res = self.get_success(
diff --git a/tests/handlers/test_directory.py b/tests/handlers/test_directory.py
index 90aec484c4..367d94eca3 100644
--- a/tests/handlers/test_directory.py
+++ b/tests/handlers/test_directory.py
@@ -13,7 +13,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 from typing import Any, Awaitable, Callable, Dict
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -27,14 +27,13 @@ from synapse.types import JsonDict, RoomAlias, create_requester
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 
 
 class DirectoryTestCase(unittest.HomeserverTestCase):
     """Tests the directory service."""
 
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
-        self.mock_federation = Mock()
+        self.mock_federation = AsyncMock()
         self.mock_registry = Mock()
 
         self.query_handlers: Dict[str, Callable[[dict], Awaitable[JsonDict]]] = {}
@@ -73,9 +72,10 @@ class DirectoryTestCase(unittest.HomeserverTestCase):
         self.assertEqual({"room_id": "!8765qwer:test", "servers": ["test"]}, result)
 
     def test_get_remote_association(self) -> None:
-        self.mock_federation.make_query.return_value = make_awaitable(
-            {"room_id": "!8765qwer:test", "servers": ["test", "remote"]}
-        )
+        self.mock_federation.make_query.return_value = {
+            "room_id": "!8765qwer:test",
+            "servers": ["test", "remote"],
+        }
 
         result = self.get_success(self.handler.get_association(self.remote_room))
 
diff --git a/tests/handlers/test_e2e_keys.py b/tests/handlers/test_e2e_keys.py
index 2eaffe511e..c5556f2844 100644
--- a/tests/handlers/test_e2e_keys.py
+++ b/tests/handlers/test_e2e_keys.py
@@ -13,7 +13,7 @@
 # WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
 # See the License for the specific language governing permissions and
 # limitations under the License.
-from typing import Iterable
+from typing import Dict, Iterable
 from unittest import mock
 
 from parameterized import parameterized
@@ -31,13 +31,12 @@ from synapse.types import JsonDict, UserID
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 from tests.unittest import override_config
 
 
 class E2eKeysHandlerTestCase(unittest.HomeserverTestCase):
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
-        self.appservice_api = mock.Mock()
+        self.appservice_api = mock.AsyncMock()
         return self.setup_test_homeserver(
             federation_client=mock.Mock(), application_service_api=self.appservice_api
         )
@@ -801,29 +800,27 @@ class E2eKeysHandlerTestCase(unittest.HomeserverTestCase):
         remote_master_key = "85T7JXPFBAySB/jwby4S3lBPTqY3+Zg53nYuGmu1ggY"
         remote_self_signing_key = "QeIiFEjluPBtI7WQdG365QKZcFs9kqmHir6RBD0//nQ"
 
-        self.hs.get_federation_client().query_client_keys = mock.Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(
-                {
-                    "device_keys": {remote_user_id: {}},
-                    "master_keys": {
-                        remote_user_id: {
-                            "user_id": remote_user_id,
-                            "usage": ["master"],
-                            "keys": {"ed25519:" + remote_master_key: remote_master_key},
+        self.hs.get_federation_client().query_client_keys = mock.AsyncMock(  # type: ignore[method-assign]
+            return_value={
+                "device_keys": {remote_user_id: {}},
+                "master_keys": {
+                    remote_user_id: {
+                        "user_id": remote_user_id,
+                        "usage": ["master"],
+                        "keys": {"ed25519:" + remote_master_key: remote_master_key},
+                    },
+                },
+                "self_signing_keys": {
+                    remote_user_id: {
+                        "user_id": remote_user_id,
+                        "usage": ["self_signing"],
+                        "keys": {
+                            "ed25519:"
+                            + remote_self_signing_key: remote_self_signing_key
                         },
-                    },
-                    "self_signing_keys": {
-                        remote_user_id: {
-                            "user_id": remote_user_id,
-                            "usage": ["self_signing"],
-                            "keys": {
-                                "ed25519:"
-                                + remote_self_signing_key: remote_self_signing_key
-                            },
-                        }
-                    },
-                }
-            )
+                    }
+                },
+            }
         )
 
         e2e_handler = self.hs.get_e2e_keys_handler()
@@ -874,34 +871,29 @@ class E2eKeysHandlerTestCase(unittest.HomeserverTestCase):
 
         # Pretend we're sharing a room with the user we're querying. If not,
         # `_query_devices_for_destination` will return early.
-        self.store.get_rooms_for_user = mock.Mock(
-            return_value=make_awaitable({"some_room_id"})
-        )
+        self.store.get_rooms_for_user = mock.AsyncMock(return_value={"some_room_id"})
 
         remote_master_key = "85T7JXPFBAySB/jwby4S3lBPTqY3+Zg53nYuGmu1ggY"
         remote_self_signing_key = "QeIiFEjluPBtI7WQdG365QKZcFs9kqmHir6RBD0//nQ"
 
-        self.hs.get_federation_client().query_user_devices = mock.Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(
-                {
+        self.hs.get_federation_client().query_user_devices = mock.AsyncMock(  # type: ignore[method-assign]
+            return_value={
+                "user_id": remote_user_id,
+                "stream_id": 1,
+                "devices": [],
+                "master_key": {
                     "user_id": remote_user_id,
-                    "stream_id": 1,
-                    "devices": [],
-                    "master_key": {
-                        "user_id": remote_user_id,
-                        "usage": ["master"],
-                        "keys": {"ed25519:" + remote_master_key: remote_master_key},
+                    "usage": ["master"],
+                    "keys": {"ed25519:" + remote_master_key: remote_master_key},
+                },
+                "self_signing_key": {
+                    "user_id": remote_user_id,
+                    "usage": ["self_signing"],
+                    "keys": {
+                        "ed25519:" + remote_self_signing_key: remote_self_signing_key
                     },
-                    "self_signing_key": {
-                        "user_id": remote_user_id,
-                        "usage": ["self_signing"],
-                        "keys": {
-                            "ed25519:"
-                            + remote_self_signing_key: remote_self_signing_key
-                        },
-                    },
-                }
-            )
+                },
+            }
         )
 
         e2e_handler = self.hs.get_e2e_keys_handler()
@@ -987,20 +979,20 @@ class E2eKeysHandlerTestCase(unittest.HomeserverTestCase):
         mock_get_rooms = mock.patch.object(
             self.store,
             "get_rooms_for_user",
-            new_callable=mock.MagicMock,
-            return_value=make_awaitable(["some_room_id"]),
+            new_callable=mock.AsyncMock,
+            return_value=["some_room_id"],
         )
         mock_get_users = mock.patch.object(
             self.store,
             "get_users_server_still_shares_room_with",
-            new_callable=mock.MagicMock,
-            return_value=make_awaitable({remote_user_id}),
+            new_callable=mock.AsyncMock,
+            return_value={remote_user_id},
         )
         mock_request = mock.patch.object(
             self.hs.get_federation_client(),
             "query_user_devices",
-            new_callable=mock.MagicMock,
-            return_value=make_awaitable(response_body),
+            new_callable=mock.AsyncMock,
+            return_value=response_body,
         )
 
         with mock_get_rooms, mock_get_users, mock_request as mocked_federation_request:
@@ -1060,8 +1052,9 @@ class E2eKeysHandlerTestCase(unittest.HomeserverTestCase):
         )
 
         # Setup a response, but only for device 2.
-        self.appservice_api.claim_client_keys.return_value = make_awaitable(
-            ({local_user: {device_id_2: otk}}, [(local_user, device_id_1, "alg1", 1)])
+        self.appservice_api.claim_client_keys.return_value = (
+            {local_user: {device_id_2: otk}},
+            [(local_user, device_id_1, "alg1", 1)],
         )
 
         # we shouldn't have any unused fallback keys yet
@@ -1127,9 +1120,10 @@ class E2eKeysHandlerTestCase(unittest.HomeserverTestCase):
         )
 
         # Setup a response.
-        self.appservice_api.claim_client_keys.return_value = make_awaitable(
-            ({local_user: {device_id_1: {**as_otk, **as_fallback_key}}}, [])
-        )
+        response: Dict[str, Dict[str, Dict[str, JsonDict]]] = {
+            local_user: {device_id_1: {**as_otk, **as_fallback_key}}
+        }
+        self.appservice_api.claim_client_keys.return_value = (response, [])
 
         # Claim OTKs, which will ask the appservice and do nothing else.
         claim_res = self.get_success(
@@ -1171,8 +1165,9 @@ class E2eKeysHandlerTestCase(unittest.HomeserverTestCase):
         self.assertEqual(fallback_res, ["alg1"])
 
         # The appservice will return only the OTK.
-        self.appservice_api.claim_client_keys.return_value = make_awaitable(
-            ({local_user: {device_id_1: as_otk}}, [])
+        self.appservice_api.claim_client_keys.return_value = (
+            {local_user: {device_id_1: as_otk}},
+            [],
         )
 
         # Claim OTKs, which should return the OTK from the appservice and the
@@ -1234,8 +1229,9 @@ class E2eKeysHandlerTestCase(unittest.HomeserverTestCase):
         self.assertEqual(fallback_res, ["alg1"])
 
         # Finally, return only the fallback key from the appservice.
-        self.appservice_api.claim_client_keys.return_value = make_awaitable(
-            ({local_user: {device_id_1: as_fallback_key}}, [])
+        self.appservice_api.claim_client_keys.return_value = (
+            {local_user: {device_id_1: as_fallback_key}},
+            [],
         )
 
         # Claim OTKs, which will return only the fallback key from the database.
@@ -1350,13 +1346,11 @@ class E2eKeysHandlerTestCase(unittest.HomeserverTestCase):
         )
 
         # Setup a response.
-        self.appservice_api.query_keys.return_value = make_awaitable(
-            {
-                "device_keys": {
-                    local_user: {device_2: device_key_2b, device_3: device_key_3}
-                }
+        self.appservice_api.query_keys.return_value = {
+            "device_keys": {
+                local_user: {device_2: device_key_2b, device_3: device_key_3}
             }
-        )
+        }
 
         # Request all devices.
         res = self.get_success(self.handler.query_local_devices({local_user: None}))
diff --git a/tests/handlers/test_federation.py b/tests/handlers/test_federation.py
index 5f11d5df11..21d63ab1f2 100644
--- a/tests/handlers/test_federation.py
+++ b/tests/handlers/test_federation.py
@@ -14,7 +14,7 @@
 import logging
 from typing import Collection, Optional, cast
 from unittest import TestCase
-from unittest.mock import Mock, patch
+from unittest.mock import AsyncMock, Mock, patch
 
 from twisted.internet.defer import Deferred
 from twisted.test.proto_helpers import MemoryReactor
@@ -40,7 +40,7 @@ from synapse.util import Clock
 from synapse.util.stringutils import random_string
 
 from tests import unittest
-from tests.test_utils import event_injection, make_awaitable
+from tests.test_utils import event_injection
 
 logger = logging.getLogger(__name__)
 
@@ -370,15 +370,15 @@ class FederationTestCase(unittest.FederatingHomeserverTestCase):
 
         # We mock out the FederationClient.backfill method, to pretend that a remote
         # server has returned our fake event.
-        federation_client_backfill_mock = Mock(return_value=make_awaitable([event]))
-        self.hs.get_federation_client().backfill = federation_client_backfill_mock  # type: ignore[assignment]
+        federation_client_backfill_mock = AsyncMock(return_value=[event])
+        self.hs.get_federation_client().backfill = federation_client_backfill_mock  # type: ignore[method-assign]
 
         # We also mock the persist method with a side effect of itself. This allows us
         # to track when it has been called while preserving its function.
         persist_events_and_notify_mock = Mock(
             side_effect=self.hs.get_federation_event_handler().persist_events_and_notify
         )
-        self.hs.get_federation_event_handler().persist_events_and_notify = (  # type: ignore[assignment]
+        self.hs.get_federation_event_handler().persist_events_and_notify = (  # type: ignore[method-assign]
             persist_events_and_notify_mock
         )
 
@@ -631,33 +631,29 @@ class PartialJoinTestCase(unittest.FederatingHomeserverTestCase):
             },
             RoomVersions.V10,
         )
-        mock_make_membership_event = Mock(
-            return_value=make_awaitable(
-                (
-                    "example.com",
-                    membership_event,
-                    RoomVersions.V10,
-                )
+        mock_make_membership_event = AsyncMock(
+            return_value=(
+                "example.com",
+                membership_event,
+                RoomVersions.V10,
             )
         )
-        mock_send_join = Mock(
-            return_value=make_awaitable(
-                SendJoinResult(
-                    membership_event,
-                    "example.com",
-                    state=[
-                        EVENT_CREATE,
-                        EVENT_CREATOR_MEMBERSHIP,
-                        EVENT_INVITATION_MEMBERSHIP,
-                    ],
-                    auth_chain=[
-                        EVENT_CREATE,
-                        EVENT_CREATOR_MEMBERSHIP,
-                        EVENT_INVITATION_MEMBERSHIP,
-                    ],
-                    partial_state=True,
-                    servers_in_room={"example.com"},
-                )
+        mock_send_join = AsyncMock(
+            return_value=SendJoinResult(
+                membership_event,
+                "example.com",
+                state=[
+                    EVENT_CREATE,
+                    EVENT_CREATOR_MEMBERSHIP,
+                    EVENT_INVITATION_MEMBERSHIP,
+                ],
+                auth_chain=[
+                    EVENT_CREATE,
+                    EVENT_CREATOR_MEMBERSHIP,
+                    EVENT_INVITATION_MEMBERSHIP,
+                ],
+                partial_state=True,
+                servers_in_room={"example.com"},
             )
         )
 
diff --git a/tests/handlers/test_federation_event.py b/tests/handlers/test_federation_event.py
index 23f1b33b2f..70e6a7e142 100644
--- a/tests/handlers/test_federation_event.py
+++ b/tests/handlers/test_federation_event.py
@@ -35,7 +35,7 @@ from synapse.types import JsonDict
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import event_injection, make_awaitable
+from tests.test_utils import event_injection
 
 
 class FederationEventHandlerTests(unittest.FederatingHomeserverTestCase):
@@ -50,6 +50,10 @@ class FederationEventHandlerTests(unittest.FederatingHomeserverTestCase):
         self.mock_federation_transport_client = mock.Mock(
             spec=["get_room_state_ids", "get_room_state", "get_event", "backfill"]
         )
+        self.mock_federation_transport_client.get_room_state_ids = mock.AsyncMock()
+        self.mock_federation_transport_client.get_room_state = mock.AsyncMock()
+        self.mock_federation_transport_client.get_event = mock.AsyncMock()
+        self.mock_federation_transport_client.backfill = mock.AsyncMock()
         return super().setup_test_homeserver(
             federation_transport_client=self.mock_federation_transport_client
         )
@@ -198,20 +202,14 @@ class FederationEventHandlerTests(unittest.FederatingHomeserverTestCase):
         )
 
         # we expect an outbound request to /state_ids, so stub that out
-        self.mock_federation_transport_client.get_room_state_ids.return_value = (
-            make_awaitable(
-                {
-                    "pdu_ids": [e.event_id for e in state_at_prev_event],
-                    "auth_chain_ids": [],
-                }
-            )
-        )
+        self.mock_federation_transport_client.get_room_state_ids.return_value = {
+            "pdu_ids": [e.event_id for e in state_at_prev_event],
+            "auth_chain_ids": [],
+        }
 
         # we also expect an outbound request to /state
         self.mock_federation_transport_client.get_room_state.return_value = (
-            make_awaitable(
-                StateRequestResponse(auth_events=[], state=state_at_prev_event)
-            )
+            StateRequestResponse(auth_events=[], state=state_at_prev_event)
         )
 
         # we have to bump the clock a bit, to keep the retry logic in
@@ -273,26 +271,23 @@ class FederationEventHandlerTests(unittest.FederatingHomeserverTestCase):
         room_version = self.get_success(main_store.get_room_version(room_id))
 
         # We expect an outbound request to /state_ids, so stub that out
-        self.mock_federation_transport_client.get_room_state_ids.return_value = make_awaitable(
-            {
-                # Mimic the other server not knowing about the state at all.
-                # We want to cause Synapse to throw an error (`Unable to get
-                # missing prev_event $fake_prev_event`) and fail to backfill
-                # the pulled event.
-                "pdu_ids": [],
-                "auth_chain_ids": [],
-            }
-        )
+        self.mock_federation_transport_client.get_room_state_ids.return_value = {
+            # Mimic the other server not knowing about the state at all.
+            # We want to cause Synapse to throw an error (`Unable to get
+            # missing prev_event $fake_prev_event`) and fail to backfill
+            # the pulled event.
+            "pdu_ids": [],
+            "auth_chain_ids": [],
+        }
+
         # We also expect an outbound request to /state
-        self.mock_federation_transport_client.get_room_state.return_value = make_awaitable(
-            StateRequestResponse(
-                # Mimic the other server not knowing about the state at all.
-                # We want to cause Synapse to throw an error (`Unable to get
-                # missing prev_event $fake_prev_event`) and fail to backfill
-                # the pulled event.
-                auth_events=[],
-                state=[],
-            )
+        self.mock_federation_transport_client.get_room_state.return_value = StateRequestResponse(
+            # Mimic the other server not knowing about the state at all.
+            # We want to cause Synapse to throw an error (`Unable to get
+            # missing prev_event $fake_prev_event`) and fail to backfill
+            # the pulled event.
+            auth_events=[],
+            state=[],
         )
 
         pulled_event = make_event_from_dict(
@@ -545,25 +540,23 @@ class FederationEventHandlerTests(unittest.FederatingHomeserverTestCase):
         )
 
         # We expect an outbound request to /backfill, so stub that out
-        self.mock_federation_transport_client.backfill.return_value = make_awaitable(
-            {
-                "origin": self.OTHER_SERVER_NAME,
-                "origin_server_ts": 123,
-                "pdus": [
-                    # This is one of the important aspects of this test: we include
-                    # `pulled_event_without_signatures` so it fails the signature check
-                    # when we filter down the backfill response down to events which
-                    # have valid signatures in
-                    # `_check_sigs_and_hash_for_pulled_events_and_fetch`
-                    pulled_event_without_signatures.get_pdu_json(),
-                    # Then later when we process this valid signature event, when we
-                    # fetch the missing `prev_event`s, we want to make sure that we
-                    # backoff and don't try and fetch `pulled_event_without_signatures`
-                    # again since we know it just had an invalid signature.
-                    pulled_event.get_pdu_json(),
-                ],
-            }
-        )
+        self.mock_federation_transport_client.backfill.return_value = {
+            "origin": self.OTHER_SERVER_NAME,
+            "origin_server_ts": 123,
+            "pdus": [
+                # This is one of the important aspects of this test: we include
+                # `pulled_event_without_signatures` so it fails the signature check
+                # when we filter down the backfill response down to events which
+                # have valid signatures in
+                # `_check_sigs_and_hash_for_pulled_events_and_fetch`
+                pulled_event_without_signatures.get_pdu_json(),
+                # Then later when we process this valid signature event, when we
+                # fetch the missing `prev_event`s, we want to make sure that we
+                # backoff and don't try and fetch `pulled_event_without_signatures`
+                # again since we know it just had an invalid signature.
+                pulled_event.get_pdu_json(),
+            ],
+        }
 
         # Keep track of the count and make sure we don't make any of these requests
         event_endpoint_requested_count = 0
@@ -731,15 +724,13 @@ class FederationEventHandlerTests(unittest.FederatingHomeserverTestCase):
         )
 
         # We expect an outbound request to /backfill, so stub that out
-        self.mock_federation_transport_client.backfill.return_value = make_awaitable(
-            {
-                "origin": self.OTHER_SERVER_NAME,
-                "origin_server_ts": 123,
-                "pdus": [
-                    pulled_event.get_pdu_json(),
-                ],
-            }
-        )
+        self.mock_federation_transport_client.backfill.return_value = {
+            "origin": self.OTHER_SERVER_NAME,
+            "origin_server_ts": 123,
+            "pdus": [
+                pulled_event.get_pdu_json(),
+            ],
+        }
 
         # The function under test: try to backfill and process the pulled event
         with LoggingContext("test"):
diff --git a/tests/handlers/test_message.py b/tests/handlers/test_message.py
index 9691d66b48..1c5897c84e 100644
--- a/tests/handlers/test_message.py
+++ b/tests/handlers/test_message.py
@@ -46,18 +46,11 @@ class EventCreationTestCase(unittest.HomeserverTestCase):
         self._persist_event_storage_controller = persistence
 
         self.user_id = self.register_user("tester", "foobar")
-        self.access_token = self.login("tester", "foobar")
-        self.room_id = self.helper.create_room_as(self.user_id, tok=self.access_token)
+        device_id = "dev-1"
+        access_token = self.login("tester", "foobar", device_id=device_id)
+        self.room_id = self.helper.create_room_as(self.user_id, tok=access_token)
 
-        info = self.get_success(
-            self.hs.get_datastores().main.get_user_by_access_token(
-                self.access_token,
-            )
-        )
-        assert info is not None
-        self.token_id = info.token_id
-
-        self.requester = create_requester(self.user_id, access_token_id=self.token_id)
+        self.requester = create_requester(self.user_id, device_id=device_id)
 
     def _create_and_persist_member_event(self) -> Tuple[EventBase, EventContext]:
         # Create a member event we can use as an auth_event
diff --git a/tests/handlers/test_oauth_delegation.py b/tests/handlers/test_oauth_delegation.py
index b891e84690..9152694653 100644
--- a/tests/handlers/test_oauth_delegation.py
+++ b/tests/handlers/test_oauth_delegation.py
@@ -39,7 +39,7 @@ from synapse.server import HomeServer
 from synapse.types import JsonDict
 from synapse.util import Clock
 
-from tests.test_utils import FakeResponse, get_awaitable_result, simple_async_mock
+from tests.test_utils import FakeResponse, get_awaitable_result
 from tests.unittest import HomeserverTestCase, skip_unless
 from tests.utils import mock_getRawHeaders
 
@@ -147,7 +147,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
     def test_inactive_token(self) -> None:
         """The handler should return a 403 where the token is inactive."""
 
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={"active": False},
@@ -166,7 +166,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
     def test_active_no_scope(self) -> None:
         """The handler should return a 403 where no scope is given."""
 
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={"active": True},
@@ -185,7 +185,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
     def test_active_user_no_subject(self) -> None:
         """The handler should return a 500 when no subject is present."""
 
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={"active": True, "scope": " ".join([MATRIX_USER_SCOPE])},
@@ -204,7 +204,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
     def test_active_no_user_scope(self) -> None:
         """The handler should return a 500 when no subject is present."""
 
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={
@@ -227,7 +227,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
     def test_active_admin_not_user(self) -> None:
         """The handler should raise when the scope has admin right but not user."""
 
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={
@@ -251,7 +251,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
     def test_active_admin(self) -> None:
         """The handler should return a requester with admin rights."""
 
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={
@@ -281,7 +281,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
     def test_active_admin_highest_privilege(self) -> None:
         """The handler should resolve to the most permissive scope."""
 
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={
@@ -313,7 +313,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
     def test_active_user(self) -> None:
         """The handler should return a requester with normal user rights."""
 
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={
@@ -344,7 +344,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
         """The handler should return a requester with normal user rights
         and an user ID matching the one specified in query param `user_id`"""
 
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={
@@ -378,7 +378,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
     def test_active_user_with_device(self) -> None:
         """The handler should return a requester with normal user rights and a device ID."""
 
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={
@@ -408,7 +408,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
     def test_multiple_devices(self) -> None:
         """The handler should raise an error if multiple devices are found in the scope."""
 
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={
@@ -433,7 +433,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
     def test_active_guest_not_allowed(self) -> None:
         """The handler should return an insufficient scope error."""
 
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={
@@ -463,7 +463,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
     def test_active_guest_allowed(self) -> None:
         """The handler should return a requester with guest user rights and a device ID."""
 
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={
@@ -499,19 +499,19 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
         request.requestHeaders.getRawHeaders = mock_getRawHeaders()
 
         # The introspection endpoint is returning an error.
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse(code=500, body=b"Internal Server Error")
         )
         error = self.get_failure(self.auth.get_user_by_req(request), SynapseError)
         self.assertEqual(error.value.code, 503)
 
         # The introspection endpoint request fails.
-        self.http_client.request = simple_async_mock(raises=Exception())
+        self.http_client.request = AsyncMock(side_effect=Exception())
         error = self.get_failure(self.auth.get_user_by_req(request), SynapseError)
         self.assertEqual(error.value.code, 503)
 
         # The introspection endpoint does not return a JSON object.
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200, payload=["this is an array", "not an object"]
             )
@@ -520,7 +520,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
         self.assertEqual(error.value.code, 503)
 
         # The introspection endpoint does not return valid JSON.
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse(code=200, body=b"this is not valid JSON")
         )
         error = self.get_failure(self.auth.get_user_by_req(request), SynapseError)
@@ -528,7 +528,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
 
     def test_introspection_token_cache(self) -> None:
         access_token = "open_sesame"
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={"active": "true", "scope": "guest", "jti": access_token},
@@ -559,7 +559,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
 
         # test that if a cached token is expired, a fresh token will be pulled from authorizing server - first add a
         # token with a soon-to-expire `exp` field to the cache
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={
@@ -640,7 +640,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
     def test_cross_signing(self) -> None:
         """Try uploading device keys with OAuth delegation enabled."""
 
-        self.http_client.request = simple_async_mock(
+        self.http_client.request = AsyncMock(
             return_value=FakeResponse.json(
                 code=200,
                 payload={
diff --git a/tests/handlers/test_oidc.py b/tests/handlers/test_oidc.py
index 0a8bae54fb..e797aaae00 100644
--- a/tests/handlers/test_oidc.py
+++ b/tests/handlers/test_oidc.py
@@ -13,7 +13,7 @@
 # limitations under the License.
 import os
 from typing import Any, Awaitable, ContextManager, Dict, Optional, Tuple
-from unittest.mock import ANY, Mock, patch
+from unittest.mock import ANY, AsyncMock, Mock, patch
 from urllib.parse import parse_qs, urlparse
 
 import pymacaroons
@@ -28,7 +28,7 @@ from synapse.util import Clock
 from synapse.util.macaroons import get_value_from_macaroon
 from synapse.util.stringutils import random_string
 
-from tests.test_utils import FakeResponse, get_awaitable_result, simple_async_mock
+from tests.test_utils import FakeResponse, get_awaitable_result
 from tests.test_utils.oidc import FakeAuthorizationGrant, FakeOidcServer
 from tests.unittest import HomeserverTestCase, override_config
 
@@ -157,15 +157,15 @@ class OidcHandlerTestCase(HomeserverTestCase):
         sso_handler = hs.get_sso_handler()
         # Mock the render error method.
         self.render_error = Mock(return_value=None)
-        sso_handler.render_error = self.render_error  # type: ignore[assignment]
+        sso_handler.render_error = self.render_error  # type: ignore[method-assign]
 
         # Reduce the number of attempts when generating MXIDs.
         sso_handler._MAP_USERNAME_RETRIES = 3
 
         auth_handler = hs.get_auth_handler()
         # Mock the complete SSO login method.
-        self.complete_sso_login = simple_async_mock()
-        auth_handler.complete_sso_login = self.complete_sso_login  # type: ignore[assignment]
+        self.complete_sso_login = AsyncMock()
+        auth_handler.complete_sso_login = self.complete_sso_login  # type: ignore[method-assign]
 
         return hs
 
diff --git a/tests/handlers/test_password_providers.py b/tests/handlers/test_password_providers.py
index 394006f5f3..11ec8c7f11 100644
--- a/tests/handlers/test_password_providers.py
+++ b/tests/handlers/test_password_providers.py
@@ -16,7 +16,7 @@
 
 from http import HTTPStatus
 from typing import Any, Dict, List, Optional, Type, Union
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -32,7 +32,6 @@ from synapse.util import Clock
 
 from tests import unittest
 from tests.server import FakeChannel
-from tests.test_utils import make_awaitable
 from tests.unittest import override_config
 
 # Login flows we expect to appear in the list after the normal ones.
@@ -187,7 +186,7 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         self.assertEqual(flows, [{"type": "m.login.password"}] + ADDITIONAL_LOGIN_FLOWS)
 
         # check_password must return an awaitable
-        mock_password_provider.check_password.return_value = make_awaitable(True)
+        mock_password_provider.check_password = AsyncMock(return_value=True)
         channel = self._send_password_login("u", "p")
         self.assertEqual(channel.code, HTTPStatus.OK, channel.result)
         self.assertEqual("@u:test", channel.json_body["user_id"])
@@ -209,13 +208,13 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         """UI Auth should delegate correctly to the password provider"""
 
         # log in twice, to get two devices
-        mock_password_provider.check_password.return_value = make_awaitable(True)
+        mock_password_provider.check_password = AsyncMock(return_value=True)
         tok1 = self.login("u", "p")
         self.login("u", "p", device_id="dev2")
         mock_password_provider.reset_mock()
 
         # have the auth provider deny the request to start with
-        mock_password_provider.check_password.return_value = make_awaitable(False)
+        mock_password_provider.check_password = AsyncMock(return_value=False)
 
         # make the initial request which returns a 401
         session = self._start_delete_device_session(tok1, "dev2")
@@ -229,7 +228,7 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         mock_password_provider.reset_mock()
 
         # Finally, check the request goes through when we allow it
-        mock_password_provider.check_password.return_value = make_awaitable(True)
+        mock_password_provider.check_password = AsyncMock(return_value=True)
         channel = self._authed_delete_device(tok1, "dev2", session, "u", "p")
         self.assertEqual(channel.code, 200)
         mock_password_provider.check_password.assert_called_once_with("@u:test", "p")
@@ -243,7 +242,7 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         self.register_user("localuser", "localpass")
 
         # check_password must return an awaitable
-        mock_password_provider.check_password.return_value = make_awaitable(False)
+        mock_password_provider.check_password = AsyncMock(return_value=False)
         channel = self._send_password_login("u", "p")
         self.assertEqual(channel.code, HTTPStatus.FORBIDDEN, channel.result)
 
@@ -260,7 +259,7 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         self.register_user("localuser", "localpass")
 
         # have the auth provider deny the request
-        mock_password_provider.check_password.return_value = make_awaitable(False)
+        mock_password_provider.check_password = AsyncMock(return_value=False)
 
         # log in twice, to get two devices
         tok1 = self.login("localuser", "localpass")
@@ -303,7 +302,7 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         self.register_user("localuser", "localpass")
 
         # check_password must return an awaitable
-        mock_password_provider.check_password.return_value = make_awaitable(False)
+        mock_password_provider.check_password = AsyncMock(return_value=False)
         channel = self._send_password_login("localuser", "localpass")
         self.assertEqual(channel.code, 403)
         self.assertEqual(channel.json_body["errcode"], "M_FORBIDDEN")
@@ -325,7 +324,7 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         self.register_user("localuser", "localpass")
 
         # allow login via the auth provider
-        mock_password_provider.check_password.return_value = make_awaitable(True)
+        mock_password_provider.check_password = AsyncMock(return_value=True)
 
         # log in twice, to get two devices
         tok1 = self.login("localuser", "p")
@@ -342,7 +341,7 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         mock_password_provider.check_password.assert_not_called()
 
         # now try deleting with the local password
-        mock_password_provider.check_password.return_value = make_awaitable(False)
+        mock_password_provider.check_password = AsyncMock(return_value=False)
         channel = self._authed_delete_device(
             tok1, "dev2", session, "localuser", "localpass"
         )
@@ -396,9 +395,7 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         self.assertEqual(channel.code, HTTPStatus.BAD_REQUEST, channel.result)
         mock_password_provider.check_auth.assert_not_called()
 
-        mock_password_provider.check_auth.return_value = make_awaitable(
-            ("@user:test", None)
-        )
+        mock_password_provider.check_auth = AsyncMock(return_value=("@user:test", None))
         channel = self._send_login("test.login_type", "u", test_field="y")
         self.assertEqual(channel.code, HTTPStatus.OK, channel.result)
         self.assertEqual("@user:test", channel.json_body["user_id"])
@@ -447,9 +444,7 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         mock_password_provider.reset_mock()
 
         # right params, but authing as the wrong user
-        mock_password_provider.check_auth.return_value = make_awaitable(
-            ("@user:test", None)
-        )
+        mock_password_provider.check_auth = AsyncMock(return_value=("@user:test", None))
         body["auth"]["test_field"] = "foo"
         channel = self._delete_device(tok1, "dev2", body)
         self.assertEqual(channel.code, 403)
@@ -460,8 +455,8 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         mock_password_provider.reset_mock()
 
         # and finally, succeed
-        mock_password_provider.check_auth.return_value = make_awaitable(
-            ("@localuser:test", None)
+        mock_password_provider.check_auth = AsyncMock(
+            return_value=("@localuser:test", None)
         )
         channel = self._delete_device(tok1, "dev2", body)
         self.assertEqual(channel.code, 200)
@@ -478,10 +473,10 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         self.custom_auth_provider_callback_test_body()
 
     def custom_auth_provider_callback_test_body(self) -> None:
-        callback = Mock(return_value=make_awaitable(None))
+        callback = AsyncMock(return_value=None)
 
-        mock_password_provider.check_auth.return_value = make_awaitable(
-            ("@user:test", callback)
+        mock_password_provider.check_auth = AsyncMock(
+            return_value=("@user:test", callback)
         )
         channel = self._send_login("test.login_type", "u", test_field="y")
         self.assertEqual(channel.code, HTTPStatus.OK, channel.result)
@@ -616,8 +611,8 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         login is disabled"""
         # register the user and log in twice via the test login type to get two devices,
         self.register_user("localuser", "localpass")
-        mock_password_provider.check_auth.return_value = make_awaitable(
-            ("@localuser:test", None)
+        mock_password_provider.check_auth = AsyncMock(
+            return_value=("@localuser:test", None)
         )
         channel = self._send_login("test.login_type", "localuser", test_field="")
         self.assertEqual(channel.code, HTTPStatus.OK, channel.result)
@@ -835,11 +830,11 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
             username: The username to use for the test.
             registration: Whether to test with registration URLs.
         """
-        self.hs.get_identity_handler().send_threepid_validation = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(0),
+        self.hs.get_identity_handler().send_threepid_validation = AsyncMock(  # type: ignore[method-assign]
+            return_value=0
         )
 
-        m = Mock(return_value=make_awaitable(False))
+        m = AsyncMock(return_value=False)
         self.hs.get_password_auth_provider().is_3pid_allowed_callbacks = [m]
 
         self.register_user(username, "password")
@@ -869,7 +864,7 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
 
         m.assert_called_once_with("email", "foo@test.com", registration)
 
-        m = Mock(return_value=make_awaitable(True))
+        m = AsyncMock(return_value=True)
         self.hs.get_password_auth_provider().is_3pid_allowed_callbacks = [m]
 
         channel = self.make_request(
diff --git a/tests/handlers/test_presence.py b/tests/handlers/test_presence.py
index 1aebcc16ad..88a16193a3 100644
--- a/tests/handlers/test_presence.py
+++ b/tests/handlers/test_presence.py
@@ -524,6 +524,7 @@ class PresenceHandlerInitTestCase(unittest.HomeserverTestCase):
 
     def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
         self.user_id = f"@test:{self.hs.config.server.server_name}"
+        self.device_id = "dev-1"
 
         # Move the reactor to the initial time.
         self.reactor.advance(1000)
@@ -608,7 +609,10 @@ class PresenceHandlerInitTestCase(unittest.HomeserverTestCase):
         self.reactor.advance(SYNC_ONLINE_TIMEOUT / 1000 / 2)
         self.get_success(
             presence_handler.user_syncing(
-                self.user_id, sync_state != PresenceState.OFFLINE, sync_state
+                self.user_id,
+                self.device_id,
+                sync_state != PresenceState.OFFLINE,
+                sync_state,
             )
         )
 
@@ -632,6 +636,7 @@ class PresenceHandlerInitTestCase(unittest.HomeserverTestCase):
 class PresenceHandlerTestCase(BaseMultiWorkerStreamTestCase):
     user_id = "@test:server"
     user_id_obj = UserID.from_string(user_id)
+    device_id = "dev-1"
 
     def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
         self.presence_handler = hs.get_presence_handler()
@@ -641,13 +646,20 @@ class PresenceHandlerTestCase(BaseMultiWorkerStreamTestCase):
         """Test that if an external process doesn't update the records for a while
         we time out their syncing users presence.
         """
-        process_id = "1"
 
-        # Notify handler that a user is now syncing.
+        # Create a worker and use it to handle /sync traffic instead.
+        # This is used to test that presence changes get replicated from workers
+        # to the main process correctly.
+        worker_to_sync_against = self.make_worker_hs(
+            "synapse.app.generic_worker", {"worker_name": "synchrotron"}
+        )
+        worker_presence_handler = worker_to_sync_against.get_presence_handler()
+
         self.get_success(
-            self.presence_handler.update_external_syncs_row(
-                process_id, self.user_id, True, self.clock.time_msec()
-            )
+            worker_presence_handler.user_syncing(
+                self.user_id, self.device_id, True, PresenceState.ONLINE
+            ),
+            by=0.1,
         )
 
         # Check that if we wait a while without telling the handler the user has
@@ -701,7 +713,7 @@ class PresenceHandlerTestCase(BaseMultiWorkerStreamTestCase):
         # Mark user as offline
         self.get_success(
             self.presence_handler.set_state(
-                self.user_id_obj, {"presence": PresenceState.OFFLINE}
+                self.user_id_obj, self.device_id, {"presence": PresenceState.OFFLINE}
             )
         )
 
@@ -733,7 +745,7 @@ class PresenceHandlerTestCase(BaseMultiWorkerStreamTestCase):
         # Mark user as online again
         self.get_success(
             self.presence_handler.set_state(
-                self.user_id_obj, {"presence": PresenceState.ONLINE}
+                self.user_id_obj, self.device_id, {"presence": PresenceState.ONLINE}
             )
         )
 
@@ -762,7 +774,7 @@ class PresenceHandlerTestCase(BaseMultiWorkerStreamTestCase):
 
         self.get_success(
             self.presence_handler.user_syncing(
-                self.user_id, False, PresenceState.ONLINE
+                self.user_id, self.device_id, False, PresenceState.ONLINE
             )
         )
 
@@ -779,7 +791,9 @@ class PresenceHandlerTestCase(BaseMultiWorkerStreamTestCase):
         self._set_presencestate_with_status_msg(PresenceState.UNAVAILABLE, status_msg)
 
         self.get_success(
-            self.presence_handler.user_syncing(self.user_id, True, PresenceState.ONLINE)
+            self.presence_handler.user_syncing(
+                self.user_id, self.device_id, True, PresenceState.ONLINE
+            )
         )
 
         state = self.get_success(self.presence_handler.get_state(self.user_id_obj))
@@ -793,7 +807,9 @@ class PresenceHandlerTestCase(BaseMultiWorkerStreamTestCase):
         self._set_presencestate_with_status_msg(PresenceState.UNAVAILABLE, status_msg)
 
         self.get_success(
-            self.presence_handler.user_syncing(self.user_id, True, PresenceState.ONLINE)
+            self.presence_handler.user_syncing(
+                self.user_id, self.device_id, True, PresenceState.ONLINE
+            )
         )
 
         state = self.get_success(self.presence_handler.get_state(self.user_id_obj))
@@ -820,7 +836,7 @@ class PresenceHandlerTestCase(BaseMultiWorkerStreamTestCase):
             # This is used to test that presence changes get replicated from workers
             # to the main process correctly.
             worker_to_sync_against = self.make_worker_hs(
-                "synapse.app.generic_worker", {"worker_name": "presence_writer"}
+                "synapse.app.generic_worker", {"worker_name": "synchrotron"}
             )
 
         # Set presence to BUSY
@@ -831,8 +847,9 @@ class PresenceHandlerTestCase(BaseMultiWorkerStreamTestCase):
         # /presence/*.
         self.get_success(
             worker_to_sync_against.get_presence_handler().user_syncing(
-                self.user_id, True, PresenceState.ONLINE
-            )
+                self.user_id, self.device_id, True, PresenceState.ONLINE
+            ),
+            by=0.1,
         )
 
         # Check against the main process that the user's presence did not change.
@@ -840,6 +857,21 @@ class PresenceHandlerTestCase(BaseMultiWorkerStreamTestCase):
         # we should still be busy
         self.assertEqual(state.state, PresenceState.BUSY)
 
+        # Advance such that the device would be discarded if it was not busy,
+        # then pump so _handle_timeouts function to called.
+        self.reactor.advance(IDLE_TIMER / 1000)
+        self.reactor.pump([5])
+
+        # The account should still be busy.
+        state = self.get_success(self.presence_handler.get_state(self.user_id_obj))
+        self.assertEqual(state.state, PresenceState.BUSY)
+
+        # Ensure that a /presence call can set the user *off* busy.
+        self._set_presencestate_with_status_msg(PresenceState.ONLINE, status_msg)
+
+        state = self.get_success(self.presence_handler.get_state(self.user_id_obj))
+        self.assertEqual(state.state, PresenceState.ONLINE)
+
     def _set_presencestate_with_status_msg(
         self, state: str, status_msg: Optional[str]
     ) -> None:
@@ -852,6 +884,7 @@ class PresenceHandlerTestCase(BaseMultiWorkerStreamTestCase):
         self.get_success(
             self.presence_handler.set_state(
                 self.user_id_obj,
+                self.device_id,
                 {"presence": state, "status_msg": status_msg},
             )
         )
@@ -876,8 +909,14 @@ class PresenceFederationQueueTestCase(unittest.HomeserverTestCase):
 
         prev_token = self.queue.get_current_token(self.instance_name)
 
-        self.queue.send_presence_to_destinations((state1, state2), ("dest1", "dest2"))
-        self.queue.send_presence_to_destinations((state3,), ("dest3",))
+        self.get_success(
+            self.queue.send_presence_to_destinations(
+                (state1, state2), ("dest1", "dest2")
+            )
+        )
+        self.get_success(
+            self.queue.send_presence_to_destinations((state3,), ("dest3",))
+        )
 
         now_token = self.queue.get_current_token(self.instance_name)
 
@@ -913,11 +952,17 @@ class PresenceFederationQueueTestCase(unittest.HomeserverTestCase):
 
         prev_token = self.queue.get_current_token(self.instance_name)
 
-        self.queue.send_presence_to_destinations((state1, state2), ("dest1", "dest2"))
+        self.get_success(
+            self.queue.send_presence_to_destinations(
+                (state1, state2), ("dest1", "dest2")
+            )
+        )
 
         now_token = self.queue.get_current_token(self.instance_name)
 
-        self.queue.send_presence_to_destinations((state3,), ("dest3",))
+        self.get_success(
+            self.queue.send_presence_to_destinations((state3,), ("dest3",))
+        )
 
         rows, upto_token, limited = self.get_success(
             self.queue.get_replication_rows("master", prev_token, now_token, 10)
@@ -956,8 +1001,14 @@ class PresenceFederationQueueTestCase(unittest.HomeserverTestCase):
 
         prev_token = self.queue.get_current_token(self.instance_name)
 
-        self.queue.send_presence_to_destinations((state1, state2), ("dest1", "dest2"))
-        self.queue.send_presence_to_destinations((state3,), ("dest3",))
+        self.get_success(
+            self.queue.send_presence_to_destinations(
+                (state1, state2), ("dest1", "dest2")
+            )
+        )
+        self.get_success(
+            self.queue.send_presence_to_destinations((state3,), ("dest3",))
+        )
 
         self.reactor.advance(10 * 60 * 1000)
 
@@ -972,8 +1023,14 @@ class PresenceFederationQueueTestCase(unittest.HomeserverTestCase):
 
         prev_token = self.queue.get_current_token(self.instance_name)
 
-        self.queue.send_presence_to_destinations((state1, state2), ("dest1", "dest2"))
-        self.queue.send_presence_to_destinations((state3,), ("dest3",))
+        self.get_success(
+            self.queue.send_presence_to_destinations(
+                (state1, state2), ("dest1", "dest2")
+            )
+        )
+        self.get_success(
+            self.queue.send_presence_to_destinations((state3,), ("dest3",))
+        )
 
         now_token = self.queue.get_current_token(self.instance_name)
 
@@ -1000,11 +1057,17 @@ class PresenceFederationQueueTestCase(unittest.HomeserverTestCase):
 
         prev_token = self.queue.get_current_token(self.instance_name)
 
-        self.queue.send_presence_to_destinations((state1, state2), ("dest1", "dest2"))
+        self.get_success(
+            self.queue.send_presence_to_destinations(
+                (state1, state2), ("dest1", "dest2")
+            )
+        )
 
         self.reactor.advance(2 * 60 * 1000)
 
-        self.queue.send_presence_to_destinations((state3,), ("dest3",))
+        self.get_success(
+            self.queue.send_presence_to_destinations((state3,), ("dest3",))
+        )
 
         self.reactor.advance(4 * 60 * 1000)
 
@@ -1020,8 +1083,14 @@ class PresenceFederationQueueTestCase(unittest.HomeserverTestCase):
 
         prev_token = self.queue.get_current_token(self.instance_name)
 
-        self.queue.send_presence_to_destinations((state1, state2), ("dest1", "dest2"))
-        self.queue.send_presence_to_destinations((state3,), ("dest3",))
+        self.get_success(
+            self.queue.send_presence_to_destinations(
+                (state1, state2), ("dest1", "dest2")
+            )
+        )
+        self.get_success(
+            self.queue.send_presence_to_destinations((state3,), ("dest3",))
+        )
 
         now_token = self.queue.get_current_token(self.instance_name)
 
@@ -1093,7 +1162,9 @@ class PresenceJoinTestCase(unittest.HomeserverTestCase):
         # Mark test2 as online, test will be offline with a last_active of 0
         self.get_success(
             self.presence_handler.set_state(
-                UserID.from_string("@test2:server"), {"presence": PresenceState.ONLINE}
+                UserID.from_string("@test2:server"),
+                "dev-1",
+                {"presence": PresenceState.ONLINE},
             )
         )
         self.reactor.pump([0])  # Wait for presence updates to be handled
@@ -1140,7 +1211,9 @@ class PresenceJoinTestCase(unittest.HomeserverTestCase):
         # Mark test as online
         self.get_success(
             self.presence_handler.set_state(
-                UserID.from_string("@test:server"), {"presence": PresenceState.ONLINE}
+                UserID.from_string("@test:server"),
+                "dev-1",
+                {"presence": PresenceState.ONLINE},
             )
         )
 
@@ -1148,7 +1221,9 @@ class PresenceJoinTestCase(unittest.HomeserverTestCase):
         # Note we don't join them to the room yet
         self.get_success(
             self.presence_handler.set_state(
-                UserID.from_string("@test2:server"), {"presence": PresenceState.ONLINE}
+                UserID.from_string("@test2:server"),
+                "dev-1",
+                {"presence": PresenceState.ONLINE},
             )
         )
 
diff --git a/tests/handlers/test_profile.py b/tests/handlers/test_profile.py
index ec2f5d30be..f9b292b9ec 100644
--- a/tests/handlers/test_profile.py
+++ b/tests/handlers/test_profile.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 from typing import Any, Awaitable, Callable, Dict
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from parameterized import parameterized
 
@@ -26,7 +26,6 @@ from synapse.types import JsonDict, UserID
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 
 
 class ProfileTestCase(unittest.HomeserverTestCase):
@@ -35,7 +34,7 @@ class ProfileTestCase(unittest.HomeserverTestCase):
     servlets = [admin.register_servlets]
 
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
-        self.mock_federation = Mock()
+        self.mock_federation = AsyncMock()
         self.mock_registry = Mock()
 
         self.query_handlers: Dict[str, Callable[[dict], Awaitable[JsonDict]]] = {}
@@ -135,9 +134,7 @@ class ProfileTestCase(unittest.HomeserverTestCase):
         )
 
     def test_get_other_name(self) -> None:
-        self.mock_federation.make_query.return_value = make_awaitable(
-            {"displayname": "Alice"}
-        )
+        self.mock_federation.make_query.return_value = {"displayname": "Alice"}
 
         displayname = self.get_success(self.handler.get_displayname(self.alice))
 
diff --git a/tests/handlers/test_register.py b/tests/handlers/test_register.py
index 54eeec228e..e9fbf32c7c 100644
--- a/tests/handlers/test_register.py
+++ b/tests/handlers/test_register.py
@@ -13,7 +13,7 @@
 # limitations under the License.
 
 from typing import Any, Collection, List, Optional, Tuple
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -38,7 +38,6 @@ from synapse.types import (
 )
 from synapse.util import Clock
 
-from tests.test_utils import make_awaitable
 from tests.unittest import override_config
 from tests.utils import mock_getRawHeaders
 
@@ -203,24 +202,22 @@ class RegistrationTestCase(unittest.HomeserverTestCase):
 
     @override_config({"limit_usage_by_mau": True})
     def test_get_or_create_user_mau_not_blocked(self) -> None:
-        self.store.count_monthly_users = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(self.hs.config.server.max_mau_value - 1)
+        self.store.count_monthly_users = AsyncMock(  # type: ignore[method-assign]
+            return_value=self.hs.config.server.max_mau_value - 1
         )
         # Ensure does not throw exception
         self.get_success(self.get_or_create_user(self.requester, "c", "User"))
 
     @override_config({"limit_usage_by_mau": True})
     def test_get_or_create_user_mau_blocked(self) -> None:
-        self.store.get_monthly_active_count = Mock(
-            return_value=make_awaitable(self.lots_of_users)
-        )
+        self.store.get_monthly_active_count = AsyncMock(return_value=self.lots_of_users)
         self.get_failure(
             self.get_or_create_user(self.requester, "b", "display_name"),
             ResourceLimitError,
         )
 
-        self.store.get_monthly_active_count = Mock(
-            return_value=make_awaitable(self.hs.config.server.max_mau_value)
+        self.store.get_monthly_active_count = AsyncMock(
+            return_value=self.hs.config.server.max_mau_value
         )
         self.get_failure(
             self.get_or_create_user(self.requester, "b", "display_name"),
@@ -229,15 +226,13 @@ class RegistrationTestCase(unittest.HomeserverTestCase):
 
     @override_config({"limit_usage_by_mau": True})
     def test_register_mau_blocked(self) -> None:
-        self.store.get_monthly_active_count = Mock(
-            return_value=make_awaitable(self.lots_of_users)
-        )
+        self.store.get_monthly_active_count = AsyncMock(return_value=self.lots_of_users)
         self.get_failure(
             self.handler.register_user(localpart="local_part"), ResourceLimitError
         )
 
-        self.store.get_monthly_active_count = Mock(
-            return_value=make_awaitable(self.hs.config.server.max_mau_value)
+        self.store.get_monthly_active_count = AsyncMock(
+            return_value=self.hs.config.server.max_mau_value
         )
         self.get_failure(
             self.handler.register_user(localpart="local_part"), ResourceLimitError
@@ -292,7 +287,7 @@ class RegistrationTestCase(unittest.HomeserverTestCase):
     @override_config({"auto_join_rooms": ["#room:test"]})
     def test_auto_create_auto_join_rooms_when_user_is_not_a_real_user(self) -> None:
         room_alias_str = "#room:test"
-        self.store.is_real_user = Mock(return_value=make_awaitable(False))
+        self.store.is_real_user = AsyncMock(return_value=False)
         user_id = self.get_success(self.handler.register_user(localpart="support"))
         rooms = self.get_success(self.store.get_rooms_for_user(user_id))
         self.assertEqual(len(rooms), 0)
@@ -304,8 +299,8 @@ class RegistrationTestCase(unittest.HomeserverTestCase):
     def test_auto_create_auto_join_rooms_when_user_is_the_first_real_user(self) -> None:
         room_alias_str = "#room:test"
 
-        self.store.count_real_users = Mock(return_value=make_awaitable(1))  # type: ignore[assignment]
-        self.store.is_real_user = Mock(return_value=make_awaitable(True))
+        self.store.count_real_users = AsyncMock(return_value=1)  # type: ignore[method-assign]
+        self.store.is_real_user = AsyncMock(return_value=True)
         user_id = self.get_success(self.handler.register_user(localpart="real"))
         rooms = self.get_success(self.store.get_rooms_for_user(user_id))
         directory_handler = self.hs.get_directory_handler()
@@ -319,8 +314,8 @@ class RegistrationTestCase(unittest.HomeserverTestCase):
     def test_auto_create_auto_join_rooms_when_user_is_not_the_first_real_user(
         self,
     ) -> None:
-        self.store.count_real_users = Mock(return_value=make_awaitable(2))  # type: ignore[assignment]
-        self.store.is_real_user = Mock(return_value=make_awaitable(True))
+        self.store.count_real_users = AsyncMock(return_value=2)  # type: ignore[method-assign]
+        self.store.is_real_user = AsyncMock(return_value=True)
         user_id = self.get_success(self.handler.register_user(localpart="real"))
         rooms = self.get_success(self.store.get_rooms_for_user(user_id))
         self.assertEqual(len(rooms), 0)
diff --git a/tests/handlers/test_room_member.py b/tests/handlers/test_room_member.py
index 41199ffa29..3e28117e2c 100644
--- a/tests/handlers/test_room_member.py
+++ b/tests/handlers/test_room_member.py
@@ -1,4 +1,4 @@
-from unittest.mock import Mock, patch
+from unittest.mock import AsyncMock, patch
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -16,7 +16,6 @@ from synapse.util import Clock
 
 from tests.replication._base import BaseMultiWorkerStreamTestCase
 from tests.server import make_request
-from tests.test_utils import make_awaitable
 from tests.unittest import (
     FederatingHomeserverTestCase,
     HomeserverTestCase,
@@ -154,25 +153,21 @@ class TestJoinsLimitedByPerRoomRateLimiter(FederatingHomeserverTestCase):
             None,
         )
 
-        mock_make_membership_event = Mock(
-            return_value=make_awaitable(
-                (
-                    self.OTHER_SERVER_NAME,
-                    join_event,
-                    self.hs.config.server.default_room_version,
-                )
+        mock_make_membership_event = AsyncMock(
+            return_value=(
+                self.OTHER_SERVER_NAME,
+                join_event,
+                self.hs.config.server.default_room_version,
             )
         )
-        mock_send_join = Mock(
-            return_value=make_awaitable(
-                SendJoinResult(
-                    join_event,
-                    self.OTHER_SERVER_NAME,
-                    state=[create_event],
-                    auth_chain=[create_event],
-                    partial_state=False,
-                    servers_in_room=frozenset(),
-                )
+        mock_send_join = AsyncMock(
+            return_value=SendJoinResult(
+                join_event,
+                self.OTHER_SERVER_NAME,
+                state=[create_event],
+                auth_chain=[create_event],
+                partial_state=False,
+                servers_in_room=frozenset(),
             )
         )
 
diff --git a/tests/handlers/test_saml.py b/tests/handlers/test_saml.py
index b5c772a7ae..00f4e181e8 100644
--- a/tests/handlers/test_saml.py
+++ b/tests/handlers/test_saml.py
@@ -13,7 +13,7 @@
 #  limitations under the License.
 
 from typing import Any, Dict, Optional, Set, Tuple
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 import attr
 
@@ -25,7 +25,6 @@ from synapse.server import HomeServer
 from synapse.types import JsonDict
 from synapse.util import Clock
 
-from tests.test_utils import simple_async_mock
 from tests.unittest import HomeserverTestCase, override_config
 
 # Check if we have the dependencies to run the tests.
@@ -134,7 +133,7 @@ class SamlHandlerTestCase(HomeserverTestCase):
 
         # stub out the auth handler
         auth_handler = self.hs.get_auth_handler()
-        auth_handler.complete_sso_login = simple_async_mock()  # type: ignore[assignment]
+        auth_handler.complete_sso_login = AsyncMock()  # type: ignore[method-assign]
 
         # send a mocked-up SAML response to the callback
         saml_response = FakeAuthnResponse({"uid": "test_user", "username": "test_user"})
@@ -164,7 +163,7 @@ class SamlHandlerTestCase(HomeserverTestCase):
 
         # stub out the auth handler
         auth_handler = self.hs.get_auth_handler()
-        auth_handler.complete_sso_login = simple_async_mock()  # type: ignore[assignment]
+        auth_handler.complete_sso_login = AsyncMock()  # type: ignore[method-assign]
 
         # Map a user via SSO.
         saml_response = FakeAuthnResponse(
@@ -206,11 +205,11 @@ class SamlHandlerTestCase(HomeserverTestCase):
 
         # stub out the auth handler
         auth_handler = self.hs.get_auth_handler()
-        auth_handler.complete_sso_login = simple_async_mock()  # type: ignore[assignment]
+        auth_handler.complete_sso_login = AsyncMock()  # type: ignore[method-assign]
 
         # mock out the error renderer too
         sso_handler = self.hs.get_sso_handler()
-        sso_handler.render_error = Mock(return_value=None)  # type: ignore[assignment]
+        sso_handler.render_error = Mock(return_value=None)  # type: ignore[method-assign]
 
         saml_response = FakeAuthnResponse({"uid": "test", "username": "föö"})
         request = _mock_request()
@@ -227,9 +226,9 @@ class SamlHandlerTestCase(HomeserverTestCase):
 
         # stub out the auth handler and error renderer
         auth_handler = self.hs.get_auth_handler()
-        auth_handler.complete_sso_login = simple_async_mock()  # type: ignore[assignment]
+        auth_handler.complete_sso_login = AsyncMock()  # type: ignore[method-assign]
         sso_handler = self.hs.get_sso_handler()
-        sso_handler.render_error = Mock(return_value=None)  # type: ignore[assignment]
+        sso_handler.render_error = Mock(return_value=None)  # type: ignore[method-assign]
 
         # register a user to occupy the first-choice MXID
         store = self.hs.get_datastores().main
@@ -312,7 +311,7 @@ class SamlHandlerTestCase(HomeserverTestCase):
 
         # stub out the auth handler
         auth_handler = self.hs.get_auth_handler()
-        auth_handler.complete_sso_login = simple_async_mock()  # type: ignore[assignment]
+        auth_handler.complete_sso_login = AsyncMock()  # type: ignore[method-assign]
 
         # The response doesn't have the proper userGroup or department.
         saml_response = FakeAuthnResponse({"uid": "test_user", "username": "test_user"})
diff --git a/tests/handlers/test_send_email.py b/tests/handlers/test_send_email.py
index 8b6e4a40b6..a066745d70 100644
--- a/tests/handlers/test_send_email.py
+++ b/tests/handlers/test_send_email.py
@@ -13,19 +13,40 @@
 # limitations under the License.
 
 
-from typing import Callable, List, Tuple
+from typing import Callable, List, Tuple, Type, Union
+from unittest.mock import patch
 
 from zope.interface import implementer
 
 from twisted.internet import defer
-from twisted.internet.address import IPv4Address
+from twisted.internet._sslverify import ClientTLSOptions
+from twisted.internet.address import IPv4Address, IPv6Address
 from twisted.internet.defer import ensureDeferred
+from twisted.internet.interfaces import IProtocolFactory
+from twisted.internet.ssl import ContextFactory
 from twisted.mail import interfaces, smtp
 
 from tests.server import FakeTransport
 from tests.unittest import HomeserverTestCase, override_config
 
 
+def TestingESMTPTLSClientFactory(
+    contextFactory: ContextFactory,
+    _connectWrapped: bool,
+    wrappedProtocol: IProtocolFactory,
+) -> IProtocolFactory:
+    """We use this to pass through in testing without using TLS, but
+    saving the context information to check that it would have happened.
+
+    Note that this is what the MemoryReactor does on connectSSL.
+    It only saves the contextFactory, but starts the connection with the
+    underlying Factory.
+    See: L{twisted.internet.testing.MemoryReactor.connectSSL}"""
+
+    wrappedProtocol._testingContextFactory = contextFactory  # type: ignore[attr-defined]
+    return wrappedProtocol
+
+
 @implementer(interfaces.IMessageDelivery)
 class _DummyMessageDelivery:
     def __init__(self) -> None:
@@ -75,7 +96,13 @@ class _DummyMessage:
         pass
 
 
-class SendEmailHandlerTestCase(HomeserverTestCase):
+class SendEmailHandlerTestCaseIPv4(HomeserverTestCase):
+    ip_class: Union[Type[IPv4Address], Type[IPv6Address]] = IPv4Address
+
+    def setUp(self) -> None:
+        super().setUp()
+        self.reactor.lookups["localhost"] = "127.0.0.1"
+
     def test_send_email(self) -> None:
         """Happy-path test that we can send email to a non-TLS server."""
         h = self.hs.get_send_email_handler()
@@ -89,7 +116,7 @@ class SendEmailHandlerTestCase(HomeserverTestCase):
         (host, port, client_factory, _timeout, _bindAddress) = self.reactor.tcpClients[
             0
         ]
-        self.assertEqual(host, "localhost")
+        self.assertEqual(host, self.reactor.lookups["localhost"])
         self.assertEqual(port, 25)
 
         # wire it up to an SMTP server
@@ -105,7 +132,9 @@ class SendEmailHandlerTestCase(HomeserverTestCase):
             FakeTransport(
                 client_protocol,
                 self.reactor,
-                peer_address=IPv4Address("TCP", "127.0.0.1", 1234),
+                peer_address=self.ip_class(
+                    "TCP", self.reactor.lookups["localhost"], 1234
+                ),
             )
         )
 
@@ -118,6 +147,10 @@ class SendEmailHandlerTestCase(HomeserverTestCase):
         self.assertEqual(str(user), "foo@bar.com")
         self.assertIn(b"Subject: test subject", msg)
 
+    @patch(
+        "synapse.handlers.send_email.TLSMemoryBIOFactory",
+        TestingESMTPTLSClientFactory,
+    )
     @override_config(
         {
             "email": {
@@ -135,17 +168,23 @@ class SendEmailHandlerTestCase(HomeserverTestCase):
             )
         )
         # there should be an attempt to connect to localhost:465
-        self.assertEqual(len(self.reactor.sslClients), 1)
+        self.assertEqual(len(self.reactor.tcpClients), 1)
         (
             host,
             port,
             client_factory,
-            contextFactory,
             _timeout,
             _bindAddress,
-        ) = self.reactor.sslClients[0]
-        self.assertEqual(host, "localhost")
+        ) = self.reactor.tcpClients[0]
+        self.assertEqual(host, self.reactor.lookups["localhost"])
         self.assertEqual(port, 465)
+        # We need to make sure that TLS is happenning
+        self.assertIsInstance(
+            client_factory._wrappedFactory._testingContextFactory,
+            ClientTLSOptions,
+        )
+        # And since we use endpoints, they go through reactor.connectTCP
+        # which works differently to connectSSL on the testing reactor
 
         # wire it up to an SMTP server
         message_delivery = _DummyMessageDelivery()
@@ -160,7 +199,9 @@ class SendEmailHandlerTestCase(HomeserverTestCase):
             FakeTransport(
                 client_protocol,
                 self.reactor,
-                peer_address=IPv4Address("TCP", "127.0.0.1", 1234),
+                peer_address=self.ip_class(
+                    "TCP", self.reactor.lookups["localhost"], 1234
+                ),
             )
         )
 
@@ -172,3 +213,11 @@ class SendEmailHandlerTestCase(HomeserverTestCase):
         user, msg = message_delivery.messages.pop()
         self.assertEqual(str(user), "foo@bar.com")
         self.assertIn(b"Subject: test subject", msg)
+
+
+class SendEmailHandlerTestCaseIPv6(SendEmailHandlerTestCaseIPv4):
+    ip_class = IPv6Address
+
+    def setUp(self) -> None:
+        super().setUp()
+        self.reactor.lookups["localhost"] = "::1"
diff --git a/tests/handlers/test_sync.py b/tests/handlers/test_sync.py
index 9f035a02dc..948d04fc32 100644
--- a/tests/handlers/test_sync.py
+++ b/tests/handlers/test_sync.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 from typing import Optional
-from unittest.mock import MagicMock, Mock, patch
+from unittest.mock import AsyncMock, Mock, patch
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -29,7 +29,6 @@ from synapse.util import Clock
 
 import tests.unittest
 import tests.utils
-from tests.test_utils import make_awaitable
 
 
 class SyncTestCase(tests.unittest.HomeserverTestCase):
@@ -253,8 +252,8 @@ class SyncTestCase(tests.unittest.HomeserverTestCase):
         mocked_get_prev_events = patch.object(
             self.hs.get_datastores().main,
             "get_prev_events_for_room",
-            new_callable=MagicMock,
-            return_value=make_awaitable([last_room_creation_event_id]),
+            new_callable=AsyncMock,
+            return_value=[last_room_creation_event_id],
         )
         with mocked_get_prev_events:
             self.helper.join(room_id, eve, tok=eve_token)
diff --git a/tests/handlers/test_typing.py b/tests/handlers/test_typing.py
index 5da1d95f0b..95106ec8f3 100644
--- a/tests/handlers/test_typing.py
+++ b/tests/handlers/test_typing.py
@@ -15,7 +15,7 @@
 
 import json
 from typing import Dict, List, Set
-from unittest.mock import ANY, Mock, call
+from unittest.mock import ANY, AsyncMock, Mock, call
 
 from netaddr import IPSet
 
@@ -33,7 +33,6 @@ from synapse.util import Clock
 
 from tests import unittest
 from tests.server import ThreadedMemoryReactorClock
-from tests.test_utils import make_awaitable
 from tests.unittest import override_config
 
 # Some local users to test with
@@ -74,11 +73,11 @@ class TypingNotificationsTestCase(unittest.HomeserverTestCase):
         # we mock out the keyring so as to skip the authentication check on the
         # federation API call.
         mock_keyring = Mock(spec=["verify_json_for_server"])
-        mock_keyring.verify_json_for_server.return_value = make_awaitable(True)
+        mock_keyring.verify_json_for_server = AsyncMock(return_value=True)
 
         # we mock out the federation client too
-        self.mock_federation_client = Mock(spec=["put_json"])
-        self.mock_federation_client.put_json.return_value = make_awaitable((200, "OK"))
+        self.mock_federation_client = AsyncMock(spec=["put_json"])
+        self.mock_federation_client.put_json.return_value = (200, "OK")
         self.mock_federation_client.agent = MatrixFederationAgent(
             reactor,
             tls_client_options_factory=None,
@@ -121,20 +120,16 @@ class TypingNotificationsTestCase(unittest.HomeserverTestCase):
 
         self.datastore = hs.get_datastores().main
 
-        self.datastore.get_destination_retry_timings = Mock(
-            return_value=make_awaitable(None)
+        self.datastore.get_device_updates_by_remote = AsyncMock(  # type: ignore[method-assign]
+            return_value=(0, [])
         )
 
-        self.datastore.get_device_updates_by_remote = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable((0, []))
+        self.datastore.get_destination_last_successful_stream_ordering = AsyncMock(  # type: ignore[method-assign]
+            return_value=None
         )
 
-        self.datastore.get_destination_last_successful_stream_ordering = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(None)
-        )
-
-        self.datastore.get_received_txn_response = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(None)
+        self.datastore.get_received_txn_response = AsyncMock(  # type: ignore[method-assign]
+            return_value=None
         )
 
         self.room_members: List[UserID] = []
@@ -146,25 +141,25 @@ class TypingNotificationsTestCase(unittest.HomeserverTestCase):
                 raise AuthError(401, "User is not in the room")
             return None
 
-        hs.get_auth().check_user_in_room = Mock(  # type: ignore[assignment]
+        hs.get_auth().check_user_in_room = Mock(  # type: ignore[method-assign]
             side_effect=check_user_in_room
         )
 
         async def check_host_in_room(room_id: str, server_name: str) -> bool:
             return room_id == ROOM_ID
 
-        hs.get_event_auth_handler().is_host_in_room = Mock(  # type: ignore[assignment]
+        hs.get_event_auth_handler().is_host_in_room = Mock(  # type: ignore[method-assign]
             side_effect=check_host_in_room
         )
 
         async def get_current_hosts_in_room(room_id: str) -> Set[str]:
             return {member.domain for member in self.room_members}
 
-        hs.get_storage_controllers().state.get_current_hosts_in_room = Mock(  # type: ignore[assignment]
+        hs.get_storage_controllers().state.get_current_hosts_in_room = Mock(  # type: ignore[method-assign]
             side_effect=get_current_hosts_in_room
         )
 
-        hs.get_storage_controllers().state.get_current_hosts_in_room_or_partial_state_approximation = Mock(  # type: ignore[assignment]
+        hs.get_storage_controllers().state.get_current_hosts_in_room_or_partial_state_approximation = Mock(  # type: ignore[method-assign]
             side_effect=get_current_hosts_in_room
         )
 
@@ -173,27 +168,25 @@ class TypingNotificationsTestCase(unittest.HomeserverTestCase):
 
         self.datastore.get_users_in_room = Mock(side_effect=get_users_in_room)
 
-        self.datastore.get_user_directory_stream_pos = Mock(  # type: ignore[assignment]
-            side_effect=(
-                # we deliberately return a non-None stream pos to avoid
-                # doing an initial_sync
-                lambda: make_awaitable(1)
-            )
+        self.datastore.get_user_directory_stream_pos = AsyncMock(  # type: ignore[method-assign]
+            # we deliberately return a non-None stream pos to avoid
+            # doing an initial_sync
+            return_value=1
         )
 
-        self.datastore.get_partial_current_state_deltas = Mock(return_value=(0, None))  # type: ignore[assignment]
+        self.datastore.get_partial_current_state_deltas = Mock(return_value=(0, None))  # type: ignore[method-assign]
 
-        self.datastore.get_to_device_stream_token = Mock(  # type: ignore[assignment]
-            side_effect=lambda: 0
+        self.datastore.get_to_device_stream_token = Mock(  # type: ignore[method-assign]
+            return_value=0
         )
-        self.datastore.get_new_device_msgs_for_remote = Mock(  # type: ignore[assignment]
-            side_effect=lambda *args, **kargs: make_awaitable(([], 0))
+        self.datastore.get_new_device_msgs_for_remote = AsyncMock(  # type: ignore[method-assign]
+            return_value=([], 0)
         )
-        self.datastore.delete_device_msgs_for_remote = Mock(  # type: ignore[assignment]
-            side_effect=lambda *args, **kargs: make_awaitable(None)
+        self.datastore.delete_device_msgs_for_remote = AsyncMock(  # type: ignore[method-assign]
+            return_value=None
         )
-        self.datastore.set_received_txn_response = Mock(  # type: ignore[assignment]
-            side_effect=lambda *args, **kwargs: make_awaitable(None)
+        self.datastore.set_received_txn_response = AsyncMock(  # type: ignore[method-assign]
+            return_value=None
         )
 
     def test_started_typing_local(self) -> None:
@@ -256,8 +249,8 @@ class TypingNotificationsTestCase(unittest.HomeserverTestCase):
             ),
             json_data_callback=ANY,
             long_retries=True,
-            backoff_on_404=True,
             try_trailing_slash_on_400=True,
+            backoff_on_all_error_codes=True,
         )
 
     def test_started_typing_remote_recv(self) -> None:
@@ -371,7 +364,7 @@ class TypingNotificationsTestCase(unittest.HomeserverTestCase):
             ),
             json_data_callback=ANY,
             long_retries=True,
-            backoff_on_404=True,
+            backoff_on_all_error_codes=True,
             try_trailing_slash_on_400=True,
         )
 
diff --git a/tests/handlers/test_user_directory.py b/tests/handlers/test_user_directory.py
index 430209705e..b5f15aa7d4 100644
--- a/tests/handlers/test_user_directory.py
+++ b/tests/handlers/test_user_directory.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 from typing import Any, Tuple
-from unittest.mock import Mock, patch
+from unittest.mock import AsyncMock, Mock, patch
 from urllib.parse import quote
 
 from twisted.test.proto_helpers import MemoryReactor
@@ -30,7 +30,7 @@ from synapse.util import Clock
 
 from tests import unittest
 from tests.storage.test_user_directory import GetUserDirectoryTables
-from tests.test_utils import event_injection, make_awaitable
+from tests.test_utils import event_injection
 from tests.test_utils.event_injection import inject_member_event
 from tests.unittest import override_config
 
@@ -471,7 +471,7 @@ class UserDirectoryTestCase(unittest.HomeserverTestCase):
             self.store.register_user(user_id=r_user_id, password_hash=None)
         )
 
-        mock_remove_from_user_dir = Mock(return_value=make_awaitable(None))
+        mock_remove_from_user_dir = AsyncMock(return_value=None)
         with patch.object(
             self.store, "remove_from_user_dir", mock_remove_from_user_dir
         ):
diff --git a/tests/http/federation/test_matrix_federation_agent.py b/tests/http/federation/test_matrix_federation_agent.py
index 6a0b5fc0bd..0d17f2fe5b 100644
--- a/tests/http/federation/test_matrix_federation_agent.py
+++ b/tests/http/federation/test_matrix_federation_agent.py
@@ -14,8 +14,8 @@
 import base64
 import logging
 import os
-from typing import Any, Awaitable, Callable, Generator, List, Optional, cast
-from unittest.mock import Mock, patch
+from typing import Generator, List, Optional, cast
+from unittest.mock import AsyncMock, patch
 
 import treq
 from netaddr import IPSet
@@ -41,7 +41,7 @@ from twisted.web.iweb import IPolicyForHTTPS, IResponse
 from synapse.config.homeserver import HomeServerConfig
 from synapse.crypto.context_factory import FederationPolicyForHTTPS
 from synapse.http.federation.matrix_federation_agent import MatrixFederationAgent
-from synapse.http.federation.srv_resolver import Server
+from synapse.http.federation.srv_resolver import Server, SrvResolver
 from synapse.http.federation.well_known_resolver import (
     WELL_KNOWN_MAX_SIZE,
     WellKnownResolver,
@@ -68,21 +68,11 @@ from tests.utils import checked_cast, default_config
 logger = logging.getLogger(__name__)
 
 
-# Once Async Mocks or lambdas are supported this can go away.
-def generate_resolve_service(
-    result: List[Server],
-) -> Callable[[Any], Awaitable[List[Server]]]:
-    async def resolve_service(_: Any) -> List[Server]:
-        return result
-
-    return resolve_service
-
-
 class MatrixFederationAgentTests(unittest.TestCase):
     def setUp(self) -> None:
         self.reactor = ThreadedMemoryReactorClock()
 
-        self.mock_resolver = Mock()
+        self.mock_resolver = AsyncMock(spec=SrvResolver)
 
         config_dict = default_config("test", parse=False)
         config_dict["federation_custom_ca_list"] = [get_test_ca_cert_file()]
@@ -636,7 +626,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
         """
         self.agent = self._make_agent()
 
-        self.mock_resolver.resolve_service.side_effect = generate_resolve_service([])
+        self.mock_resolver.resolve_service.return_value = []
         self.reactor.lookups["testserv1"] = "1.2.3.4"
 
         test_d = self._make_get_request(b"matrix-federation://testserv1/foo/bar")
@@ -722,7 +712,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
         """
         self.agent = self._make_agent()
 
-        self.mock_resolver.resolve_service.side_effect = generate_resolve_service([])
+        self.mock_resolver.resolve_service.return_value = []
         self.reactor.lookups["testserv"] = "1.2.3.4"
 
         test_d = self._make_get_request(b"matrix-federation://testserv/foo/bar")
@@ -776,7 +766,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
         """Test the behaviour when the .well-known delegates elsewhere"""
         self.agent = self._make_agent()
 
-        self.mock_resolver.resolve_service.side_effect = generate_resolve_service([])
+        self.mock_resolver.resolve_service.return_value = []
         self.reactor.lookups["testserv"] = "1.2.3.4"
         self.reactor.lookups["target-server"] = "1::f"
 
@@ -840,7 +830,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
         """
         self.agent = self._make_agent()
 
-        self.mock_resolver.resolve_service.side_effect = generate_resolve_service([])
+        self.mock_resolver.resolve_service.return_value = []
         self.reactor.lookups["testserv"] = "1.2.3.4"
         self.reactor.lookups["target-server"] = "1::f"
 
@@ -930,7 +920,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
         """
         self.agent = self._make_agent()
 
-        self.mock_resolver.resolve_service.side_effect = generate_resolve_service([])
+        self.mock_resolver.resolve_service.return_value = []
         self.reactor.lookups["testserv"] = "1.2.3.4"
 
         test_d = self._make_get_request(b"matrix-federation://testserv/foo/bar")
@@ -986,7 +976,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
         # the config left to the default, which will not trust it (since the
         # presented cert is signed by a test CA)
 
-        self.mock_resolver.resolve_service.side_effect = generate_resolve_service([])
+        self.mock_resolver.resolve_service.return_value = []
         self.reactor.lookups["testserv"] = "1.2.3.4"
 
         config = default_config("test", parse=True)
@@ -1037,9 +1027,9 @@ class MatrixFederationAgentTests(unittest.TestCase):
         """
         self.agent = self._make_agent()
 
-        self.mock_resolver.resolve_service.side_effect = generate_resolve_service(
-            [Server(host=b"srvtarget", port=8443)]
-        )
+        self.mock_resolver.resolve_service.return_value = [
+            Server(host=b"srvtarget", port=8443)
+        ]
         self.reactor.lookups["srvtarget"] = "1.2.3.4"
 
         test_d = self._make_get_request(b"matrix-federation://testserv/foo/bar")
@@ -1094,9 +1084,9 @@ class MatrixFederationAgentTests(unittest.TestCase):
         self.assertEqual(host, "1.2.3.4")
         self.assertEqual(port, 443)
 
-        self.mock_resolver.resolve_service.side_effect = generate_resolve_service(
-            [Server(host=b"srvtarget", port=8443)]
-        )
+        self.mock_resolver.resolve_service.return_value = [
+            Server(host=b"srvtarget", port=8443)
+        ]
 
         self._handle_well_known_connection(
             client_factory,
@@ -1137,7 +1127,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
         """test the behaviour when the server name has idna chars in"""
         self.agent = self._make_agent()
 
-        self.mock_resolver.resolve_service.side_effect = generate_resolve_service([])
+        self.mock_resolver.resolve_service.return_value = []
 
         # the resolver is always called with the IDNA hostname as a native string.
         self.reactor.lookups["xn--bcher-kva.com"] = "1.2.3.4"
@@ -1201,9 +1191,9 @@ class MatrixFederationAgentTests(unittest.TestCase):
         """test the behaviour when the target of a SRV record has idna chars"""
         self.agent = self._make_agent()
 
-        self.mock_resolver.resolve_service.side_effect = generate_resolve_service(
-            [Server(host=b"xn--trget-3qa.com", port=8443)]  # târget.com
-        )
+        self.mock_resolver.resolve_service.return_value = [
+            Server(host=b"xn--trget-3qa.com", port=8443)
+        ]  # târget.com
         self.reactor.lookups["xn--trget-3qa.com"] = "1.2.3.4"
 
         test_d = self._make_get_request(
@@ -1407,12 +1397,10 @@ class MatrixFederationAgentTests(unittest.TestCase):
         """Test that other SRV results are tried if the first one fails."""
         self.agent = self._make_agent()
 
-        self.mock_resolver.resolve_service.side_effect = generate_resolve_service(
-            [
-                Server(host=b"target.com", port=8443),
-                Server(host=b"target.com", port=8444),
-            ]
-        )
+        self.mock_resolver.resolve_service.return_value = [
+            Server(host=b"target.com", port=8443),
+            Server(host=b"target.com", port=8444),
+        ]
         self.reactor.lookups["target.com"] = "1.2.3.4"
 
         test_d = self._make_get_request(b"matrix-federation://testserv/foo/bar")
diff --git a/tests/logging/test_terse_json.py b/tests/logging/test_terse_json.py
index fa27f1279a..c379853e20 100644
--- a/tests/logging/test_terse_json.py
+++ b/tests/logging/test_terse_json.py
@@ -164,7 +164,7 @@ class TerseJsonTestCase(LoggerCleanupMixin, TestCase):
         # Call requestReceived to finish instantiating the object.
         request.content = BytesIO()
         # Partially skip some internal processing of SynapseRequest.
-        request._started_processing = Mock()  # type: ignore[assignment]
+        request._started_processing = Mock()  # type: ignore[method-assign]
         request.request_metrics = Mock(spec=["name"])
         with patch.object(Request, "render"):
             request.requestReceived(b"POST", b"/_matrix/client/versions", b"1.1")
diff --git a/tests/module_api/test_api.py b/tests/module_api/test_api.py
index fe631d7ecb..172fc3a736 100644
--- a/tests/module_api/test_api.py
+++ b/tests/module_api/test_api.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 from typing import Any, Dict, Optional
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from twisted.internet import defer
 from twisted.test.proto_helpers import MemoryReactor
@@ -33,7 +33,6 @@ from synapse.util import Clock
 
 from tests.events.test_presence_router import send_presence_update, sync_presence
 from tests.replication._base import BaseMultiWorkerStreamTestCase
-from tests.test_utils import simple_async_mock
 from tests.test_utils.event_injection import inject_member_event
 from tests.unittest import HomeserverTestCase, override_config
 
@@ -70,7 +69,7 @@ class ModuleApiTestCase(BaseModuleApiTestCase):
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
         # Mock out the calls over federation.
         self.fed_transport_client = Mock(spec=["send_transaction"])
-        self.fed_transport_client.send_transaction = simple_async_mock({})
+        self.fed_transport_client.send_transaction = AsyncMock(return_value={})
 
         return self.setup_test_homeserver(
             federation_transport_client=self.fed_transport_client,
@@ -234,7 +233,7 @@ class ModuleApiTestCase(BaseModuleApiTestCase):
     def test_sending_events_into_room(self) -> None:
         """Tests that a module can send events into a room"""
         # Mock out create_and_send_nonmember_event to check whether events are being sent
-        self.event_creation_handler.create_and_send_nonmember_event = Mock(  # type: ignore[assignment]
+        self.event_creation_handler.create_and_send_nonmember_event = Mock(  # type: ignore[method-assign]
             spec=[],
             side_effect=self.event_creation_handler.create_and_send_nonmember_event,
         )
@@ -579,10 +578,8 @@ class ModuleApiTestCase(BaseModuleApiTestCase):
         """Test that the module API can join a remote room."""
         # Necessary to fake a remote join.
         fake_stream_id = 1
-        mocked_remote_join = simple_async_mock(
-            return_value=("fake-event-id", fake_stream_id)
-        )
-        self.hs.get_room_member_handler()._remote_join = mocked_remote_join  # type: ignore[assignment]
+        mocked_remote_join = AsyncMock(return_value=("fake-event-id", fake_stream_id))
+        self.hs.get_room_member_handler()._remote_join = mocked_remote_join  # type: ignore[method-assign]
         fake_remote_host = f"{self.module_api.server_name}-remote"
 
         # Given that the join is to be faked, we expect the relevant join event not to
diff --git a/tests/push/test_bulk_push_rule_evaluator.py b/tests/push/test_bulk_push_rule_evaluator.py
index 829b9df83d..7c23b77e0a 100644
--- a/tests/push/test_bulk_push_rule_evaluator.py
+++ b/tests/push/test_bulk_push_rule_evaluator.py
@@ -13,7 +13,7 @@
 # limitations under the License.
 
 from typing import Any, Optional
-from unittest.mock import patch
+from unittest.mock import AsyncMock, patch
 
 from parameterized import parameterized
 
@@ -28,7 +28,6 @@ from synapse.server import HomeServer
 from synapse.types import JsonDict, create_requester
 from synapse.util import Clock
 
-from tests.test_utils import simple_async_mock
 from tests.unittest import HomeserverTestCase, override_config
 
 
@@ -191,7 +190,7 @@ class TestBulkPushRuleEvaluator(HomeserverTestCase):
         # Mock the method which calculates push rules -- we do this instead of
         # e.g. checking the results in the database because we want to ensure
         # that code isn't even running.
-        bulk_evaluator._action_for_event_by_user = simple_async_mock()  # type: ignore[assignment]
+        bulk_evaluator._action_for_event_by_user = AsyncMock()  # type: ignore[method-assign]
 
         # Ensure no actions are generated!
         self.get_success(bulk_evaluator.action_for_events_by_user([(event, context)]))
@@ -382,7 +381,6 @@ class TestBulkPushRuleEvaluator(HomeserverTestCase):
             )
         )
 
-    @override_config({"experimental_features": {"msc3958_supress_edit_notifs": True}})
     def test_suppress_edits(self) -> None:
         """Under the default push rules, event edits should not generate notifications."""
         bulk_evaluator = BulkPushRuleEvaluator(self.hs)
diff --git a/tests/replication/storage/test_events.py b/tests/replication/storage/test_events.py
index f7c6417a09..af25815fa5 100644
--- a/tests/replication/storage/test_events.py
+++ b/tests/replication/storage/test_events.py
@@ -58,7 +58,7 @@ def patch__eq__(cls: object) -> Callable[[], None]:
 
     def unpatch() -> None:
         if eq is not None:
-            cls.__eq__ = eq  # type: ignore[assignment]
+            cls.__eq__ = eq  # type: ignore[method-assign]
 
     return unpatch
 
diff --git a/tests/replication/test_federation_sender_shard.py b/tests/replication/test_federation_sender_shard.py
index a324b4d31d..9b28cd474f 100644
--- a/tests/replication/test_federation_sender_shard.py
+++ b/tests/replication/test_federation_sender_shard.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 import logging
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from netaddr import IPSet
 
@@ -26,7 +26,6 @@ from synapse.types import UserID, create_requester
 
 from tests.replication._base import BaseMultiWorkerStreamTestCase
 from tests.server import get_clock
-from tests.test_utils import make_awaitable
 
 logger = logging.getLogger(__name__)
 
@@ -62,7 +61,7 @@ class FederationSenderTestCase(BaseMultiWorkerStreamTestCase):
         new event.
         """
         mock_client = Mock(spec=["put_json"])
-        mock_client.put_json.return_value = make_awaitable({})
+        mock_client.put_json = AsyncMock(return_value={})
         mock_client.agent = self.matrix_federation_agent
         self.make_worker_hs(
             "synapse.app.generic_worker",
@@ -93,7 +92,7 @@ class FederationSenderTestCase(BaseMultiWorkerStreamTestCase):
         new events.
         """
         mock_client1 = Mock(spec=["put_json"])
-        mock_client1.put_json.return_value = make_awaitable({})
+        mock_client1.put_json = AsyncMock(return_value={})
         mock_client1.agent = self.matrix_federation_agent
         self.make_worker_hs(
             "synapse.app.generic_worker",
@@ -108,7 +107,7 @@ class FederationSenderTestCase(BaseMultiWorkerStreamTestCase):
         )
 
         mock_client2 = Mock(spec=["put_json"])
-        mock_client2.put_json.return_value = make_awaitable({})
+        mock_client2.put_json = AsyncMock(return_value={})
         mock_client2.agent = self.matrix_federation_agent
         self.make_worker_hs(
             "synapse.app.generic_worker",
@@ -162,7 +161,7 @@ class FederationSenderTestCase(BaseMultiWorkerStreamTestCase):
         new typing EDUs.
         """
         mock_client1 = Mock(spec=["put_json"])
-        mock_client1.put_json.return_value = make_awaitable({})
+        mock_client1.put_json = AsyncMock(return_value={})
         mock_client1.agent = self.matrix_federation_agent
         self.make_worker_hs(
             "synapse.app.generic_worker",
@@ -177,7 +176,7 @@ class FederationSenderTestCase(BaseMultiWorkerStreamTestCase):
         )
 
         mock_client2 = Mock(spec=["put_json"])
-        mock_client2.put_json.return_value = make_awaitable({})
+        mock_client2.put_json = AsyncMock(return_value={})
         mock_client2.agent = self.matrix_federation_agent
         self.make_worker_hs(
             "synapse.app.generic_worker",
diff --git a/tests/rest/admin/test_user.py b/tests/rest/admin/test_user.py
index feb81844ae..761871b933 100644
--- a/tests/rest/admin/test_user.py
+++ b/tests/rest/admin/test_user.py
@@ -18,7 +18,7 @@ import os
 import urllib.parse
 from binascii import unhexlify
 from typing import List, Optional
-from unittest.mock import Mock, patch
+from unittest.mock import AsyncMock, Mock, patch
 
 from parameterized import parameterized, parameterized_class
 
@@ -40,12 +40,13 @@ from synapse.rest.client import (
     user_directory,
 )
 from synapse.server import HomeServer
+from synapse.storage.databases.main.client_ips import LAST_SEEN_GRANULARITY
 from synapse.types import JsonDict, UserID, create_requester
 from synapse.util import Clock
 
 from tests import unittest
 from tests.server import FakeSite, make_request
-from tests.test_utils import SMALL_PNG, make_awaitable
+from tests.test_utils import SMALL_PNG
 from tests.unittest import override_config
 
 
@@ -71,8 +72,8 @@ class UserRegisterTestCase(unittest.HomeserverTestCase):
 
         self.hs.config.registration.registration_shared_secret = "shared"
 
-        self.hs.get_media_repository = Mock()  # type: ignore[assignment]
-        self.hs.get_deactivate_account_handler = Mock()  # type: ignore[assignment]
+        self.hs.get_media_repository = Mock()  # type: ignore[method-assign]
+        self.hs.get_deactivate_account_handler = Mock()  # type: ignore[method-assign]
 
         return self.hs
 
@@ -419,8 +420,8 @@ class UserRegisterTestCase(unittest.HomeserverTestCase):
         store = self.hs.get_datastores().main
 
         # Set monthly active users to the limit
-        store.get_monthly_active_count = Mock(
-            return_value=make_awaitable(self.hs.config.server.max_mau_value)
+        store.get_monthly_active_count = AsyncMock(
+            return_value=self.hs.config.server.max_mau_value
         )
         # Check that the blocking of monthly active users is working as expected
         # The registration of a new user fails due to the limit
@@ -456,6 +457,7 @@ class UsersListTestCase(unittest.HomeserverTestCase):
     servlets = [
         synapse.rest.admin.register_servlets,
         login.register_servlets,
+        room.register_servlets,
     ]
     url = "/_synapse/admin/v2/users"
 
@@ -506,6 +508,62 @@ class UsersListTestCase(unittest.HomeserverTestCase):
         # Check that all fields are available
         self._check_fields(channel.json_body["users"])
 
+    def test_last_seen(self) -> None:
+        """
+        Test that last_seen_ts field is properly working.
+        """
+        user1 = self.register_user("u1", "pass")
+        user1_token = self.login("u1", "pass")
+        user2 = self.register_user("u2", "pass")
+        user2_token = self.login("u2", "pass")
+        user3 = self.register_user("u3", "pass")
+        user3_token = self.login("u3", "pass")
+
+        self.helper.create_room_as(self.admin_user, tok=self.admin_user_tok)
+        self.reactor.advance(10)
+        self.helper.create_room_as(user2, tok=user2_token)
+        self.reactor.advance(10)
+        self.helper.create_room_as(user1, tok=user1_token)
+        self.reactor.advance(10)
+        self.helper.create_room_as(user3, tok=user3_token)
+        self.reactor.advance(10)
+
+        channel = self.make_request(
+            "GET",
+            self.url,
+            access_token=self.admin_user_tok,
+        )
+
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+        self.assertEqual(4, len(channel.json_body["users"]))
+        self.assertEqual(4, channel.json_body["total"])
+
+        admin_last_seen = channel.json_body["users"][0]["last_seen_ts"]
+        user1_last_seen = channel.json_body["users"][1]["last_seen_ts"]
+        user2_last_seen = channel.json_body["users"][2]["last_seen_ts"]
+        user3_last_seen = channel.json_body["users"][3]["last_seen_ts"]
+        self.assertTrue(admin_last_seen > 0 and admin_last_seen < 10000)
+        self.assertTrue(user2_last_seen > 10000 and user2_last_seen < 20000)
+        self.assertTrue(user1_last_seen > 20000 and user1_last_seen < 30000)
+        self.assertTrue(user3_last_seen > 30000 and user3_last_seen < 40000)
+
+        self._order_test([self.admin_user, user2, user1, user3], "last_seen_ts")
+
+        self.reactor.advance(LAST_SEEN_GRANULARITY / 1000)
+        self.helper.create_room_as(user1, tok=user1_token)
+        self.reactor.advance(10)
+
+        channel = self.make_request(
+            "GET",
+            self.url + "/" + user1,
+            access_token=self.admin_user_tok,
+        )
+        self.assertTrue(
+            channel.json_body["last_seen_ts"] > 40000 + LAST_SEEN_GRANULARITY
+        )
+
+        self._order_test([self.admin_user, user2, user3, user1], "last_seen_ts")
+
     def test_search_term(self) -> None:
         """Test that searching for a users works correctly"""
 
@@ -1135,6 +1193,7 @@ class UsersListTestCase(unittest.HomeserverTestCase):
             self.assertIn("displayname", u)
             self.assertIn("avatar_url", u)
             self.assertIn("creation_ts", u)
+            self.assertIn("last_seen_ts", u)
 
     def _create_users(self, number_users: int) -> None:
         """
@@ -1834,8 +1893,8 @@ class UserRestTestCase(unittest.HomeserverTestCase):
             )
 
         # Set monthly active users to the limit
-        self.store.get_monthly_active_count = Mock(
-            return_value=make_awaitable(self.hs.config.server.max_mau_value)
+        self.store.get_monthly_active_count = AsyncMock(
+            return_value=self.hs.config.server.max_mau_value
         )
         # Check that the blocking of monthly active users is working as expected
         # The registration of a new user fails due to the limit
@@ -1871,8 +1930,8 @@ class UserRestTestCase(unittest.HomeserverTestCase):
         handler = self.hs.get_registration_handler()
 
         # Set monthly active users to the limit
-        self.store.get_monthly_active_count = Mock(
-            return_value=make_awaitable(self.hs.config.server.max_mau_value)
+        self.store.get_monthly_active_count = AsyncMock(
+            return_value=self.hs.config.server.max_mau_value
         )
         # Check that the blocking of monthly active users is working as expected
         # The registration of a new user fails due to the limit
@@ -3035,6 +3094,7 @@ class UserRestTestCase(unittest.HomeserverTestCase):
         self.assertIn("consent_version", content)
         self.assertIn("consent_ts", content)
         self.assertIn("external_ids", content)
+        self.assertIn("last_seen_ts", content)
 
         # This key was removed intentionally. Ensure it is not accidentally re-included.
         self.assertNotIn("password_hash", content)
diff --git a/tests/rest/admin/test_username_available.py b/tests/rest/admin/test_username_available.py
index 6c04e6c56c..4c69d224b8 100644
--- a/tests/rest/admin/test_username_available.py
+++ b/tests/rest/admin/test_username_available.py
@@ -50,7 +50,7 @@ class UsernameAvailableTestCase(unittest.HomeserverTestCase):
             )
 
         handler = self.hs.get_registration_handler()
-        handler.check_username = check_username  # type: ignore[assignment]
+        handler.check_username = check_username  # type: ignore[method-assign]
 
     def test_username_available(self) -> None:
         """
diff --git a/tests/rest/client/test_account.py b/tests/rest/client/test_account.py
index ac19f3c6da..e9f495e206 100644
--- a/tests/rest/client/test_account.py
+++ b/tests/rest/client/test_account.py
@@ -1346,7 +1346,7 @@ class AccountStatusTestCase(unittest.HomeserverTestCase):
                 return {}
 
         # Register a mock that will return the expected result depending on the remote.
-        self.hs.get_federation_http_client().post_json = Mock(side_effect=post_json)  # type: ignore[assignment]
+        self.hs.get_federation_http_client().post_json = Mock(side_effect=post_json)  # type: ignore[method-assign]
 
         # Check that we've got the correct response from the client-side endpoint.
         self._test_status(
diff --git a/tests/rest/client/test_account_data.py b/tests/rest/client/test_account_data.py
index d5b0640e7a..481db9a687 100644
--- a/tests/rest/client/test_account_data.py
+++ b/tests/rest/client/test_account_data.py
@@ -11,13 +11,12 @@
 # WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
 # See the License for the specific language governing permissions and
 # limitations under the License.
-from unittest.mock import Mock
+from unittest.mock import AsyncMock
 
 from synapse.rest import admin
 from synapse.rest.client import account_data, login, room
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 
 
 class AccountDataTestCase(unittest.HomeserverTestCase):
@@ -32,7 +31,7 @@ class AccountDataTestCase(unittest.HomeserverTestCase):
         """Tests that the on_account_data_updated module callback is called correctly when
         a user's account data changes.
         """
-        mocked_callback = Mock(return_value=make_awaitable(None))
+        mocked_callback = AsyncMock(return_value=None)
         self.hs.get_account_data_handler()._on_account_data_updated_callbacks.append(
             mocked_callback
         )
diff --git a/tests/rest/client/test_events.py b/tests/rest/client/test_events.py
index 54df2a252c..141e0f57a3 100644
--- a/tests/rest/client/test_events.py
+++ b/tests/rest/client/test_events.py
@@ -45,7 +45,7 @@ class EventStreamPermissionsTestCase(unittest.HomeserverTestCase):
 
         hs = self.setup_test_homeserver(config=config)
 
-        hs.get_federation_handler = Mock()  # type: ignore[assignment]
+        hs.get_federation_handler = Mock()  # type: ignore[method-assign]
 
         return hs
 
diff --git a/tests/rest/client/test_filter.py b/tests/rest/client/test_filter.py
index a2d5d340be..90a8df147c 100644
--- a/tests/rest/client/test_filter.py
+++ b/tests/rest/client/test_filter.py
@@ -65,14 +65,14 @@ class FilterTestCase(unittest.HomeserverTestCase):
 
     def test_add_filter_non_local_user(self) -> None:
         _is_mine = self.hs.is_mine
-        self.hs.is_mine = lambda target_user: False  # type: ignore[assignment]
+        self.hs.is_mine = lambda target_user: False  # type: ignore[method-assign]
         channel = self.make_request(
             "POST",
             "/_matrix/client/r0/user/%s/filter" % (self.user_id),
             self.EXAMPLE_FILTER_JSON,
         )
 
-        self.hs.is_mine = _is_mine  # type: ignore[assignment]
+        self.hs.is_mine = _is_mine  # type: ignore[method-assign]
         self.assertEqual(channel.code, 403)
         self.assertEqual(channel.json_body["errcode"], Codes.FORBIDDEN)
 
diff --git a/tests/rest/client/test_login.py b/tests/rest/client/test_login.py
index ffbc13bb8d..a2a6589564 100644
--- a/tests/rest/client/test_login.py
+++ b/tests/rest/client/test_login.py
@@ -169,7 +169,8 @@ class LoginRestServletTestCase(unittest.HomeserverTestCase):
                 # which sets these values to 10000, but as we're overriding the entire
                 # rc_login dict here, we need to set this manually as well
                 "account": {"per_second": 10000, "burst_count": 10000},
-            }
+            },
+            "experimental_features": {"msc4041_enabled": True},
         }
     )
     def test_POST_ratelimiting_per_address(self) -> None:
@@ -189,12 +190,15 @@ class LoginRestServletTestCase(unittest.HomeserverTestCase):
             if i == 5:
                 self.assertEqual(channel.code, 429, msg=channel.result)
                 retry_after_ms = int(channel.json_body["retry_after_ms"])
+                retry_header = channel.headers.getRawHeaders("Retry-After")
             else:
                 self.assertEqual(channel.code, 200, msg=channel.result)
 
         # Since we're ratelimiting at 1 request/min, retry_after_ms should be lower
         # than 1min.
-        self.assertTrue(retry_after_ms < 6000)
+        self.assertLess(retry_after_ms, 6000)
+        assert retry_header
+        self.assertLessEqual(int(retry_header[0]), 6)
 
         self.reactor.advance(retry_after_ms / 1000.0 + 1.0)
 
@@ -217,7 +221,8 @@ class LoginRestServletTestCase(unittest.HomeserverTestCase):
                 # which sets these values to 10000, but as we're overriding the entire
                 # rc_login dict here, we need to set this manually as well
                 "address": {"per_second": 10000, "burst_count": 10000},
-            }
+            },
+            "experimental_features": {"msc4041_enabled": True},
         }
     )
     def test_POST_ratelimiting_per_account(self) -> None:
@@ -234,12 +239,15 @@ class LoginRestServletTestCase(unittest.HomeserverTestCase):
             if i == 5:
                 self.assertEqual(channel.code, 429, msg=channel.result)
                 retry_after_ms = int(channel.json_body["retry_after_ms"])
+                retry_header = channel.headers.getRawHeaders("Retry-After")
             else:
                 self.assertEqual(channel.code, 200, msg=channel.result)
 
         # Since we're ratelimiting at 1 request/min, retry_after_ms should be lower
         # than 1min.
-        self.assertTrue(retry_after_ms < 6000)
+        self.assertLess(retry_after_ms, 6000)
+        assert retry_header
+        self.assertLessEqual(int(retry_header[0]), 6)
 
         self.reactor.advance(retry_after_ms / 1000.0)
 
@@ -262,7 +270,8 @@ class LoginRestServletTestCase(unittest.HomeserverTestCase):
                 # rc_login dict here, we need to set this manually as well
                 "address": {"per_second": 10000, "burst_count": 10000},
                 "failed_attempts": {"per_second": 0.17, "burst_count": 5},
-            }
+            },
+            "experimental_features": {"msc4041_enabled": True},
         }
     )
     def test_POST_ratelimiting_per_account_failed_attempts(self) -> None:
@@ -279,12 +288,15 @@ class LoginRestServletTestCase(unittest.HomeserverTestCase):
             if i == 5:
                 self.assertEqual(channel.code, 429, msg=channel.result)
                 retry_after_ms = int(channel.json_body["retry_after_ms"])
+                retry_header = channel.headers.getRawHeaders("Retry-After")
             else:
                 self.assertEqual(channel.code, 403, msg=channel.result)
 
         # Since we're ratelimiting at 1 request/min, retry_after_ms should be lower
         # than 1min.
-        self.assertTrue(retry_after_ms < 6000)
+        self.assertLess(retry_after_ms, 6000)
+        assert retry_header
+        self.assertLessEqual(int(retry_header[0]), 6)
 
         self.reactor.advance(retry_after_ms / 1000.0 + 1.0)
 
@@ -569,8 +581,9 @@ class LoginRestServletTestCase(unittest.HomeserverTestCase):
             body,
         )
         self.assertEqual(channel.code, 403, channel.result)
-        self.assertDictContainsSubset(
-            {"errcode": Codes.LIMIT_EXCEEDED, "extra": "value"}, channel.json_body
+        self.assertLessEqual(
+            {"errcode": Codes.LIMIT_EXCEEDED, "extra": "value"}.items(),
+            channel.json_body.items(),
         )
 
 
diff --git a/tests/rest/client/test_notifications.py b/tests/rest/client/test_notifications.py
index 700f6587a0..41ceb3db51 100644
--- a/tests/rest/client/test_notifications.py
+++ b/tests/rest/client/test_notifications.py
@@ -11,7 +11,7 @@
 # WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
 # See the License for the specific language governing permissions and
 # limitations under the License.
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -20,7 +20,6 @@ from synapse.rest.client import login, notifications, receipts, room
 from synapse.server import HomeServer
 from synapse.util import Clock
 
-from tests.test_utils import simple_async_mock
 from tests.unittest import HomeserverTestCase
 
 
@@ -45,7 +44,7 @@ class HTTPPusherTests(HomeserverTestCase):
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
         # Mock out the calls over federation.
         fed_transport_client = Mock(spec=["send_transaction"])
-        fed_transport_client.send_transaction = simple_async_mock({})
+        fed_transport_client.send_transaction = AsyncMock(return_value={})
 
         return self.setup_test_homeserver(
             federation_transport_client=fed_transport_client,
diff --git a/tests/rest/client/test_presence.py b/tests/rest/client/test_presence.py
index e12098102b..66b387cea3 100644
--- a/tests/rest/client/test_presence.py
+++ b/tests/rest/client/test_presence.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 from http import HTTPStatus
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -23,7 +23,6 @@ from synapse.types import UserID
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 
 
 class PresenceTestCase(unittest.HomeserverTestCase):
@@ -36,7 +35,7 @@ class PresenceTestCase(unittest.HomeserverTestCase):
 
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
         self.presence_handler = Mock(spec=PresenceHandler)
-        self.presence_handler.set_state.return_value = make_awaitable(None)
+        self.presence_handler.set_state = AsyncMock(return_value=None)
 
         hs = self.setup_test_homeserver(
             "red",
diff --git a/tests/rest/client/test_register.py b/tests/rest/client/test_register.py
index b228dba861..c33393dc28 100644
--- a/tests/rest/client/test_register.py
+++ b/tests/rest/client/test_register.py
@@ -75,7 +75,7 @@ class RegisterRestServletTestCase(unittest.HomeserverTestCase):
 
         self.assertEqual(channel.code, 200, msg=channel.result)
         det_data = {"user_id": user_id, "home_server": self.hs.hostname}
-        self.assertDictContainsSubset(det_data, channel.json_body)
+        self.assertLessEqual(det_data.items(), channel.json_body.items())
 
     def test_POST_appservice_registration_no_type(self) -> None:
         as_token = "i_am_an_app_service"
@@ -136,7 +136,7 @@ class RegisterRestServletTestCase(unittest.HomeserverTestCase):
             "device_id": device_id,
         }
         self.assertEqual(channel.code, 200, msg=channel.result)
-        self.assertDictContainsSubset(det_data, channel.json_body)
+        self.assertLessEqual(det_data.items(), channel.json_body.items())
 
     @override_config({"enable_registration": False})
     def test_POST_disabled_registration(self) -> None:
@@ -157,7 +157,7 @@ class RegisterRestServletTestCase(unittest.HomeserverTestCase):
 
         det_data = {"home_server": self.hs.hostname, "device_id": "guest_device"}
         self.assertEqual(channel.code, 200, msg=channel.result)
-        self.assertDictContainsSubset(det_data, channel.json_body)
+        self.assertLessEqual(det_data.items(), channel.json_body.items())
 
     def test_POST_disabled_guest_registration(self) -> None:
         self.hs.config.registration.allow_guest_access = False
@@ -267,7 +267,7 @@ class RegisterRestServletTestCase(unittest.HomeserverTestCase):
             "device_id": device_id,
         }
         self.assertEqual(channel.code, 200, msg=channel.result)
-        self.assertDictContainsSubset(det_data, channel.json_body)
+        self.assertLessEqual(det_data.items(), channel.json_body.items())
 
         # Check the `completed` counter has been incremented and pending is 0
         res = self.get_success(
diff --git a/tests/rest/client/test_relations.py b/tests/rest/client/test_relations.py
index 9bfe913e45..61773fb28c 100644
--- a/tests/rest/client/test_relations.py
+++ b/tests/rest/client/test_relations.py
@@ -15,7 +15,7 @@
 
 import urllib.parse
 from typing import Any, Callable, Dict, List, Optional, Tuple
-from unittest.mock import patch
+from unittest.mock import AsyncMock, patch
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -28,7 +28,6 @@ from synapse.util import Clock
 
 from tests import unittest
 from tests.server import FakeChannel
-from tests.test_utils import make_awaitable
 from tests.test_utils.event_injection import inject_event
 from tests.unittest import override_config
 
@@ -264,7 +263,8 @@ class RelationsTestCase(BaseRelationsTestCase):
         # Disable the validation to pretend this came over federation.
         with patch(
             "synapse.handlers.message.EventCreationHandler._validate_event_relation",
-            new=lambda self, event: make_awaitable(None),
+            new_callable=AsyncMock,
+            return_value=None,
         ):
             # Generate a various relations from a different room.
             self.get_success(
@@ -570,7 +570,7 @@ class RelationsTestCase(BaseRelationsTestCase):
         )
         self.assertEqual(200, channel.code, channel.json_body)
         event_result = channel.json_body
-        self.assertDictContainsSubset(original_body, event_result["content"])
+        self.assertLessEqual(original_body.items(), event_result["content"].items())
 
         # also check /context, which returns the *edited* event
         channel = self.make_request(
@@ -587,14 +587,14 @@ class RelationsTestCase(BaseRelationsTestCase):
             (context_result, "/context"),
         ):
             # The reference metadata should still be intact.
-            self.assertDictContainsSubset(
+            self.assertLessEqual(
                 {
                     "m.relates_to": {
                         "event_id": self.parent_id,
                         "rel_type": "m.reference",
                     }
-                },
-                result_event_dict["content"],
+                }.items(),
+                result_event_dict["content"].items(),
                 desc,
             )
 
@@ -1300,7 +1300,8 @@ class BundledAggregationsTestCase(BaseRelationsTestCase):
         # not an event the Client-Server API will allow..
         with patch(
             "synapse.handlers.message.EventCreationHandler._validate_event_relation",
-            new=lambda self, event: make_awaitable(None),
+            new_callable=AsyncMock,
+            return_value=None,
         ):
             # Create a sub-thread off the thread, which is not allowed.
             self._send_relation(
@@ -1371,9 +1372,11 @@ class BundledAggregationsTestCase(BaseRelationsTestCase):
         latest_event_in_thread = thread_summary["latest_event"]
         # The latest event in the thread should have the edit appear under the
         # bundled aggregations.
-        self.assertDictContainsSubset(
-            {"event_id": edit_event_id, "sender": "@alice:test"},
-            latest_event_in_thread["unsigned"]["m.relations"][RelationTypes.REPLACE],
+        self.assertLessEqual(
+            {"event_id": edit_event_id, "sender": "@alice:test"}.items(),
+            latest_event_in_thread["unsigned"]["m.relations"][
+                RelationTypes.REPLACE
+            ].items(),
         )
 
     def test_aggregation_get_event_for_annotation(self) -> None:
@@ -1636,9 +1639,9 @@ class RelationRedactionTestCase(BaseRelationsTestCase):
         ##################################################
         self.assertEqual(self._get_related_events(), list(reversed(thread_replies)))
         relations = self._get_bundled_aggregations()
-        self.assertDictContainsSubset(
-            {"count": 3, "current_user_participated": True},
-            relations[RelationTypes.THREAD],
+        self.assertLessEqual(
+            {"count": 3, "current_user_participated": True}.items(),
+            relations[RelationTypes.THREAD].items(),
         )
         # The latest event is the last sent event.
         self.assertEqual(
@@ -1657,9 +1660,9 @@ class RelationRedactionTestCase(BaseRelationsTestCase):
         # The thread should still exist, but the latest event should be updated.
         self.assertEqual(self._get_related_events(), list(reversed(thread_replies)))
         relations = self._get_bundled_aggregations()
-        self.assertDictContainsSubset(
-            {"count": 2, "current_user_participated": True},
-            relations[RelationTypes.THREAD],
+        self.assertLessEqual(
+            {"count": 2, "current_user_participated": True}.items(),
+            relations[RelationTypes.THREAD].items(),
         )
         # And the latest event is the last unredacted event.
         self.assertEqual(
@@ -1676,9 +1679,9 @@ class RelationRedactionTestCase(BaseRelationsTestCase):
         # Nothing should have changed (except the thread count).
         self.assertEqual(self._get_related_events(), thread_replies)
         relations = self._get_bundled_aggregations()
-        self.assertDictContainsSubset(
-            {"count": 1, "current_user_participated": True},
-            relations[RelationTypes.THREAD],
+        self.assertLessEqual(
+            {"count": 1, "current_user_participated": True}.items(),
+            relations[RelationTypes.THREAD].items(),
         )
         # And the latest event is the last unredacted event.
         self.assertEqual(
@@ -1773,12 +1776,12 @@ class RelationRedactionTestCase(BaseRelationsTestCase):
         event_ids = self._get_related_events()
         relations = self._get_bundled_aggregations()
         self.assertEqual(len(event_ids), 1)
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "count": 1,
                 "current_user_participated": True,
-            },
-            relations[RelationTypes.THREAD],
+            }.items(),
+            relations[RelationTypes.THREAD].items(),
         )
         self.assertEqual(
             relations[RelationTypes.THREAD]["latest_event"]["event_id"],
diff --git a/tests/rest/client/test_rooms.py b/tests/rest/client/test_rooms.py
index 88e579dc39..47c1d38ad7 100644
--- a/tests/rest/client/test_rooms.py
+++ b/tests/rest/client/test_rooms.py
@@ -20,7 +20,7 @@
 import json
 from http import HTTPStatus
 from typing import Any, Dict, Iterable, List, Optional, Tuple, Union
-from unittest.mock import Mock, call, patch
+from unittest.mock import AsyncMock, Mock, call, patch
 from urllib import parse as urlparse
 
 from parameterized import param, parameterized
@@ -52,7 +52,6 @@ from synapse.util.stringutils import random_string
 from tests import unittest
 from tests.http.server._base import make_request_with_cancellation_test
 from tests.storage.test_stream import PaginationTestCase
-from tests.test_utils import make_awaitable
 from tests.test_utils.event_injection import create_event
 from tests.unittest import override_config
 
@@ -69,15 +68,15 @@ class RoomBase(unittest.HomeserverTestCase):
             "red",
         )
 
-        self.hs.get_federation_handler = Mock()  # type: ignore[assignment]
-        self.hs.get_federation_handler.return_value.maybe_backfill = Mock(
-            return_value=make_awaitable(None)
+        self.hs.get_federation_handler = Mock()  # type: ignore[method-assign]
+        self.hs.get_federation_handler.return_value.maybe_backfill = AsyncMock(
+            return_value=None
         )
 
         async def _insert_client_ip(*args: Any, **kwargs: Any) -> None:
             return None
 
-        self.hs.get_datastores().main.insert_client_ip = _insert_client_ip  # type: ignore[assignment]
+        self.hs.get_datastores().main.insert_client_ip = _insert_client_ip  # type: ignore[method-assign]
 
         return self.hs
 
@@ -2375,7 +2374,7 @@ class PublicRoomsTestRemoteSearchFallbackTestCase(unittest.HomeserverTestCase):
     ]
 
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
-        return self.setup_test_homeserver(federation_client=Mock())
+        return self.setup_test_homeserver(federation_client=AsyncMock())
 
     def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
         self.register_user("user", "pass")
@@ -2385,7 +2384,7 @@ class PublicRoomsTestRemoteSearchFallbackTestCase(unittest.HomeserverTestCase):
 
     def test_simple(self) -> None:
         "Simple test for searching rooms over federation"
-        self.federation_client.get_public_rooms.return_value = make_awaitable({})  # type: ignore[attr-defined]
+        self.federation_client.get_public_rooms.return_value = {}  # type: ignore[attr-defined]
 
         search_filter = {PublicRoomsFilterFields.GENERIC_SEARCH_TERM: "foobar"}
 
@@ -2413,7 +2412,7 @@ class PublicRoomsTestRemoteSearchFallbackTestCase(unittest.HomeserverTestCase):
         # with a 404, when using search filters.
         self.federation_client.get_public_rooms.side_effect = (  # type: ignore[attr-defined]
             HttpResponseException(HTTPStatus.NOT_FOUND, "Not Found", b""),
-            make_awaitable({}),
+            {},
         )
 
         search_filter = {PublicRoomsFilterFields.GENERIC_SEARCH_TERM: "foobar"}
@@ -3413,17 +3412,17 @@ class ThreepidInviteTestCase(unittest.HomeserverTestCase):
         # Mock a few functions to prevent the test from failing due to failing to talk to
         # a remote IS. We keep the mock for make_and_store_3pid_invite around so we
         # can check its call_count later on during the test.
-        make_invite_mock = Mock(return_value=make_awaitable((Mock(event_id="abc"), 0)))
-        self.hs.get_room_member_handler()._make_and_store_3pid_invite = make_invite_mock  # type: ignore[assignment]
-        self.hs.get_identity_handler().lookup_3pid = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(None),
+        make_invite_mock = AsyncMock(return_value=(Mock(event_id="abc"), 0))
+        self.hs.get_room_member_handler()._make_and_store_3pid_invite = make_invite_mock  # type: ignore[method-assign]
+        self.hs.get_identity_handler().lookup_3pid = AsyncMock(  # type: ignore[method-assign]
+            return_value=None,
         )
 
         # Add a mock to the spamchecker callbacks for user_may_send_3pid_invite. Make it
         # allow everything for now.
         # `spec` argument is needed for this function mock to have `__qualname__`, which
         # is needed for `Measure` metrics buried in SpamChecker.
-        mock = Mock(return_value=make_awaitable(True), spec=lambda *x: None)
+        mock = AsyncMock(return_value=True, spec=lambda *x: None)
         self.hs.get_module_api_callbacks().spam_checker._user_may_send_3pid_invite_callbacks.append(
             mock
         )
@@ -3451,7 +3450,7 @@ class ThreepidInviteTestCase(unittest.HomeserverTestCase):
 
         # Now change the return value of the callback to deny any invite and test that
         # we can't send the invite.
-        mock.return_value = make_awaitable(False)
+        mock.return_value = False
         channel = self.make_request(
             method="POST",
             path="/rooms/" + self.room_id + "/invite",
@@ -3477,18 +3476,18 @@ class ThreepidInviteTestCase(unittest.HomeserverTestCase):
         # Mock a few functions to prevent the test from failing due to failing to talk to
         # a remote IS. We keep the mock for make_and_store_3pid_invite around so we
         # can check its call_count later on during the test.
-        make_invite_mock = Mock(return_value=make_awaitable((Mock(event_id="abc"), 0)))
-        self.hs.get_room_member_handler()._make_and_store_3pid_invite = make_invite_mock  # type: ignore[assignment]
-        self.hs.get_identity_handler().lookup_3pid = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(None),
+        make_invite_mock = AsyncMock(return_value=(Mock(event_id="abc"), 0))
+        self.hs.get_room_member_handler()._make_and_store_3pid_invite = make_invite_mock  # type: ignore[method-assign]
+        self.hs.get_identity_handler().lookup_3pid = AsyncMock(  # type: ignore[method-assign]
+            return_value=None,
         )
 
         # Add a mock to the spamchecker callbacks for user_may_send_3pid_invite. Make it
         # allow everything for now.
         # `spec` argument is needed for this function mock to have `__qualname__`, which
         # is needed for `Measure` metrics buried in SpamChecker.
-        mock = Mock(
-            return_value=make_awaitable(synapse.module_api.NOT_SPAM),
+        mock = AsyncMock(
+            return_value=synapse.module_api.NOT_SPAM,
             spec=lambda *x: None,
         )
         self.hs.get_module_api_callbacks().spam_checker._user_may_send_3pid_invite_callbacks.append(
@@ -3519,7 +3518,7 @@ class ThreepidInviteTestCase(unittest.HomeserverTestCase):
         # Now change the return value of the callback to deny any invite and test that
         # we can't send the invite. We pick an arbitrary error code to be able to check
         # that the same code has been returned
-        mock.return_value = make_awaitable(Codes.CONSENT_NOT_GIVEN)
+        mock.return_value = Codes.CONSENT_NOT_GIVEN
         channel = self.make_request(
             method="POST",
             path="/rooms/" + self.room_id + "/invite",
@@ -3538,7 +3537,7 @@ class ThreepidInviteTestCase(unittest.HomeserverTestCase):
         make_invite_mock.assert_called_once()
 
         # Run variant with `Tuple[Codes, dict]`.
-        mock.return_value = make_awaitable((Codes.EXPIRED_ACCOUNT, {"field": "value"}))
+        mock.return_value = (Codes.EXPIRED_ACCOUNT, {"field": "value"})
         channel = self.make_request(
             method="POST",
             path="/rooms/" + self.room_id + "/invite",
diff --git a/tests/rest/client/test_shadow_banned.py b/tests/rest/client/test_shadow_banned.py
index 8d2cdf8751..9aecf88e41 100644
--- a/tests/rest/client/test_shadow_banned.py
+++ b/tests/rest/client/test_shadow_banned.py
@@ -84,7 +84,7 @@ class RoomTestCase(_ShadowBannedBase):
     def test_invite_3pid(self) -> None:
         """Ensure that a 3PID invite does not attempt to contact the identity server."""
         identity_handler = self.hs.get_identity_handler()
-        identity_handler.lookup_3pid = Mock(  # type: ignore[assignment]
+        identity_handler.lookup_3pid = Mock(  # type: ignore[method-assign]
             side_effect=AssertionError("This should not get called")
         )
 
diff --git a/tests/rest/client/test_third_party_rules.py b/tests/rest/client/test_third_party_rules.py
index e5ba5a9706..57eb713b15 100644
--- a/tests/rest/client/test_third_party_rules.py
+++ b/tests/rest/client/test_third_party_rules.py
@@ -13,7 +13,7 @@
 # limitations under the License.
 import threading
 from typing import TYPE_CHECKING, Any, Dict, Optional, Tuple, Union
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -33,7 +33,6 @@ from synapse.util import Clock
 from synapse.util.frozenutils import unfreeze
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 
 if TYPE_CHECKING:
     from synapse.module_api import ModuleApi
@@ -118,7 +117,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         async def _check_event_auth(origin: Any, event: Any, context: Any) -> None:
             pass
 
-        hs.get_federation_event_handler()._check_event_auth = _check_event_auth  # type: ignore[assignment]
+        hs.get_federation_event_handler()._check_event_auth = _check_event_auth  # type: ignore[method-assign]
 
         return hs
 
@@ -477,7 +476,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
 
     def test_on_new_event(self) -> None:
         """Test that the on_new_event callback is called on new events"""
-        on_new_event = Mock(make_awaitable(None))
+        on_new_event = AsyncMock(return_value=None)
         self.hs.get_module_api_callbacks().third_party_event_rules._on_new_event_callbacks.append(
             on_new_event
         )
@@ -580,7 +579,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         avatar_url = "mxc://matrix.org/oWQDvfewxmlRaRCkVbfetyEo"
 
         # Register a mock callback.
-        m = Mock(return_value=make_awaitable(None))
+        m = AsyncMock(return_value=None)
         self.hs.get_module_api_callbacks().third_party_event_rules._on_profile_update_callbacks.append(
             m
         )
@@ -641,7 +640,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         avatar_url = "mxc://matrix.org/oWQDvfewxmlRaRCkVbfetyEo"
 
         # Register a mock callback.
-        m = Mock(return_value=make_awaitable(None))
+        m = AsyncMock(return_value=None)
         self.hs.get_module_api_callbacks().third_party_event_rules._on_profile_update_callbacks.append(
             m
         )
@@ -682,7 +681,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         correctly when processing a user's deactivation.
         """
         # Register a mocked callback.
-        deactivation_mock = Mock(return_value=make_awaitable(None))
+        deactivation_mock = AsyncMock(return_value=None)
         third_party_rules = self.hs.get_module_api_callbacks().third_party_event_rules
         third_party_rules._on_user_deactivation_status_changed_callbacks.append(
             deactivation_mock,
@@ -690,7 +689,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         # Also register a mocked callback for profile updates, to check that the
         # deactivation code calls it in a way that let modules know the user is being
         # deactivated.
-        profile_mock = Mock(return_value=make_awaitable(None))
+        profile_mock = AsyncMock(return_value=None)
         self.hs.get_module_api_callbacks().third_party_event_rules._on_profile_update_callbacks.append(
             profile_mock,
         )
@@ -740,7 +739,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         well as a reactivation.
         """
         # Register a mock callback.
-        m = Mock(return_value=make_awaitable(None))
+        m = AsyncMock(return_value=None)
         third_party_rules = self.hs.get_module_api_callbacks().third_party_event_rules
         third_party_rules._on_user_deactivation_status_changed_callbacks.append(m)
 
@@ -794,7 +793,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         correctly when processing a user's deactivation.
         """
         # Register a mocked callback.
-        deactivation_mock = Mock(return_value=make_awaitable(False))
+        deactivation_mock = AsyncMock(return_value=False)
         third_party_rules = self.hs.get_module_api_callbacks().third_party_event_rules
         third_party_rules._check_can_deactivate_user_callbacks.append(
             deactivation_mock,
@@ -840,7 +839,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         correctly when processing a user's deactivation triggered by a server admin.
         """
         # Register a mocked callback.
-        deactivation_mock = Mock(return_value=make_awaitable(False))
+        deactivation_mock = AsyncMock(return_value=False)
         third_party_rules = self.hs.get_module_api_callbacks().third_party_event_rules
         third_party_rules._check_can_deactivate_user_callbacks.append(
             deactivation_mock,
@@ -879,7 +878,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         correctly when processing an admin's shutdown room request.
         """
         # Register a mocked callback.
-        shutdown_mock = Mock(return_value=make_awaitable(False))
+        shutdown_mock = AsyncMock(return_value=False)
         third_party_rules = self.hs.get_module_api_callbacks().third_party_event_rules
         third_party_rules._check_can_shutdown_room_callbacks.append(
             shutdown_mock,
@@ -915,7 +914,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         associating a 3PID to an account.
         """
         # Register a mocked callback.
-        threepid_bind_mock = Mock(return_value=make_awaitable(None))
+        threepid_bind_mock = AsyncMock(return_value=None)
         third_party_rules = self.hs.get_module_api_callbacks().third_party_event_rules
         third_party_rules._on_threepid_bind_callbacks.append(threepid_bind_mock)
 
@@ -957,11 +956,9 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         just before associating and removing a 3PID to/from an account.
         """
         # Pretend to be a Synapse module and register both callbacks as mocks.
-        on_add_user_third_party_identifier_callback_mock = Mock(
-            return_value=make_awaitable(None)
-        )
-        on_remove_user_third_party_identifier_callback_mock = Mock(
-            return_value=make_awaitable(None)
+        on_add_user_third_party_identifier_callback_mock = AsyncMock(return_value=None)
+        on_remove_user_third_party_identifier_callback_mock = AsyncMock(
+            return_value=None
         )
         self.hs.get_module_api().register_third_party_rules_callbacks(
             on_add_user_third_party_identifier=on_add_user_third_party_identifier_callback_mock,
@@ -1021,8 +1018,8 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         when a user is deactivated and their third-party ID associations are deleted.
         """
         # Pretend to be a Synapse module and register both callbacks as mocks.
-        on_remove_user_third_party_identifier_callback_mock = Mock(
-            return_value=make_awaitable(None)
+        on_remove_user_third_party_identifier_callback_mock = AsyncMock(
+            return_value=None
         )
         self.hs.get_module_api().register_third_party_rules_callbacks(
             on_remove_user_third_party_identifier=on_remove_user_third_party_identifier_callback_mock,
diff --git a/tests/rest/client/test_transactions.py b/tests/rest/client/test_transactions.py
index d8dc56261a..951a3cbc43 100644
--- a/tests/rest/client/test_transactions.py
+++ b/tests/rest/client/test_transactions.py
@@ -14,7 +14,7 @@
 
 from http import HTTPStatus
 from typing import Any, Generator, Tuple, cast
-from unittest.mock import Mock, call
+from unittest.mock import AsyncMock, Mock, call
 
 from twisted.internet import defer, reactor as _reactor
 
@@ -24,7 +24,6 @@ from synapse.types import ISynapseReactor, JsonDict
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 from tests.utils import MockClock
 
 reactor = cast(ISynapseReactor, _reactor)
@@ -53,7 +52,7 @@ class HttpTransactionCacheTestCase(unittest.TestCase):
     def test_executes_given_function(
         self,
     ) -> Generator["defer.Deferred[Any]", object, None]:
-        cb = Mock(return_value=make_awaitable(self.mock_http_response))
+        cb = AsyncMock(return_value=self.mock_http_response)
         res = yield self.cache.fetch_or_execute_request(
             self.mock_request, self.mock_requester, cb, "some_arg", keyword="arg"
         )
@@ -64,7 +63,7 @@ class HttpTransactionCacheTestCase(unittest.TestCase):
     def test_deduplicates_based_on_key(
         self,
     ) -> Generator["defer.Deferred[Any]", object, None]:
-        cb = Mock(return_value=make_awaitable(self.mock_http_response))
+        cb = AsyncMock(return_value=self.mock_http_response)
         for i in range(3):  # invoke multiple times
             res = yield self.cache.fetch_or_execute_request(
                 self.mock_request,
@@ -168,7 +167,7 @@ class HttpTransactionCacheTestCase(unittest.TestCase):
 
     @defer.inlineCallbacks
     def test_cleans_up(self) -> Generator["defer.Deferred[Any]", object, None]:
-        cb = Mock(return_value=make_awaitable(self.mock_http_response))
+        cb = AsyncMock(return_value=self.mock_http_response)
         yield self.cache.fetch_or_execute_request(
             self.mock_request, self.mock_requester, cb, "an arg"
         )
diff --git a/tests/server.py b/tests/server.py
index ff03d28864..08633fe640 100644
--- a/tests/server.py
+++ b/tests/server.py
@@ -12,6 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 import hashlib
+import ipaddress
 import json
 import logging
 import os
@@ -45,7 +46,7 @@ import attr
 from typing_extensions import ParamSpec
 from zope.interface import implementer
 
-from twisted.internet import address, threads, udp
+from twisted.internet import address, tcp, threads, udp
 from twisted.internet._resolver import SimpleResolverComplexifier
 from twisted.internet.defer import Deferred, fail, maybeDeferred, succeed
 from twisted.internet.error import DNSLookupError
@@ -567,6 +568,8 @@ class ThreadedMemoryReactorClock(MemoryReactorClock):
         conn = super().connectTCP(
             host, port, factory, timeout=timeout, bindAddress=None
         )
+        if self.lookups and host in self.lookups:
+            validate_connector(conn, self.lookups[host])
 
         callback = self._tcp_callbacks.get((host, port))
         if callback:
@@ -599,6 +602,55 @@ class ThreadedMemoryReactorClock(MemoryReactorClock):
             super().advance(0)
 
 
+def validate_connector(connector: tcp.Connector, expected_ip: str) -> None:
+    """Try to validate the obtained connector as it would happen when
+    synapse is running and the conection will be established.
+
+    This method will raise a useful exception when necessary, else it will
+    just do nothing.
+
+    This is in order to help catch quirks related to reactor.connectTCP,
+    since when called directly, the connector's destination will be of type
+    IPv4Address, with the hostname as the literal host that was given (which
+    could be an IPv6-only host or an IPv6 literal).
+
+    But when called from reactor.connectTCP *through* e.g. an Endpoint, the
+    connector's destination will contain the specific IP address with the
+    correct network stack class.
+
+    Note that testing code paths that use connectTCP directly should not be
+    affected by this check, unless they specifically add a test with a
+    matching reactor.lookups[HOSTNAME] = "IPv6Literal", where reactor is of
+    type ThreadedMemoryReactorClock.
+    For an example of implementing such tests, see test/handlers/send_email.py.
+    """
+    destination = connector.getDestination()
+
+    # We use address.IPv{4,6}Address to check what the reactor thinks it is
+    # is sending but check for validity with ipaddress.IPv{4,6}Address
+    # because they fail with IPs on the wrong network stack.
+    cls_mapping = {
+        address.IPv4Address: ipaddress.IPv4Address,
+        address.IPv6Address: ipaddress.IPv6Address,
+    }
+
+    cls = cls_mapping.get(destination.__class__)
+
+    if cls is not None:
+        try:
+            cls(expected_ip)
+        except Exception as exc:
+            raise ValueError(
+                "Invalid IP type and resolution for %s. Expected %s to be %s"
+                % (destination, expected_ip, cls.__name__)
+            ) from exc
+    else:
+        raise ValueError(
+            "Unknown address type %s for %s"
+            % (destination.__class__.__name__, destination)
+        )
+
+
 class ThreadPool:
     """
     Threadless thread pool.
@@ -670,7 +722,7 @@ def _make_test_homeserver_synchronous(server: HomeServer) -> None:
                 **kwargs,
             )
 
-        pool.runWithConnection = runWithConnection  # type: ignore[assignment]
+        pool.runWithConnection = runWithConnection  # type: ignore[method-assign]
         pool.runInteraction = runInteraction  # type: ignore[assignment]
         # Replace the thread pool with a threadless 'thread' pool
         pool.threadpool = ThreadPool(clock._reactor)
diff --git a/tests/server_notices/test_resource_limits_server_notices.py b/tests/server_notices/test_resource_limits_server_notices.py
index d2bfa53eda..17f428bfc5 100644
--- a/tests/server_notices/test_resource_limits_server_notices.py
+++ b/tests/server_notices/test_resource_limits_server_notices.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 from typing import Tuple
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -29,7 +29,6 @@ from synapse.types import JsonDict
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 from tests.unittest import override_config
 from tests.utils import default_config
 
@@ -69,24 +68,22 @@ class TestResourceLimitsServerNotices(unittest.HomeserverTestCase):
         assert isinstance(rlsn, ResourceLimitsServerNotices)
         self._rlsn = rlsn
 
-        self._rlsn._store.user_last_seen_monthly_active = Mock(
-            return_value=make_awaitable(1000)
-        )
-        self._rlsn._server_notices_manager.send_notice = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(Mock())
+        self._rlsn._store.user_last_seen_monthly_active = AsyncMock(return_value=1000)
+        self._rlsn._server_notices_manager.send_notice = AsyncMock(  # type: ignore[method-assign]
+            return_value=Mock()
         )
         self._send_notice = self._rlsn._server_notices_manager.send_notice
 
         self.user_id = "@user_id:test"
 
-        self._rlsn._server_notices_manager.get_or_create_notice_room_for_user = Mock(
-            return_value=make_awaitable("!something:localhost")
+        self._rlsn._server_notices_manager.get_or_create_notice_room_for_user = (
+            AsyncMock(return_value="!something:localhost")
         )
-        self._rlsn._server_notices_manager.maybe_get_notice_room_for_user = Mock(
-            return_value=make_awaitable("!something:localhost")
+        self._rlsn._server_notices_manager.maybe_get_notice_room_for_user = AsyncMock(
+            return_value="!something:localhost"
         )
-        self._rlsn._store.add_tag_to_room = Mock(return_value=make_awaitable(None))  # type: ignore[assignment]
-        self._rlsn._store.get_tags_for_room = Mock(return_value=make_awaitable({}))  # type: ignore[assignment]
+        self._rlsn._store.add_tag_to_room = AsyncMock(return_value=None)  # type: ignore[method-assign]
+        self._rlsn._store.get_tags_for_room = AsyncMock(return_value={})  # type: ignore[method-assign]
 
     @override_config({"hs_disabled": True})
     def test_maybe_send_server_notice_disabled_hs(self) -> None:
@@ -103,14 +100,14 @@ class TestResourceLimitsServerNotices(unittest.HomeserverTestCase):
     def test_maybe_send_server_notice_to_user_remove_blocked_notice(self) -> None:
         """Test when user has blocked notice, but should have it removed"""
 
-        self._rlsn._auth_blocking.check_auth_blocking = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(None)
+        self._rlsn._auth_blocking.check_auth_blocking = AsyncMock(  # type: ignore[method-assign]
+            return_value=None
         )
         mock_event = Mock(
             type=EventTypes.Message, content={"msgtype": ServerNoticeMsgType}
         )
-        self._rlsn._store.get_events = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable({"123": mock_event})
+        self._rlsn._store.get_events = AsyncMock(  # type: ignore[method-assign]
+            return_value={"123": mock_event}
         )
         self.get_success(self._rlsn.maybe_send_server_notice_to_user(self.user_id))
         # Would be better to check the content, but once == remove blocking event
@@ -125,16 +122,16 @@ class TestResourceLimitsServerNotices(unittest.HomeserverTestCase):
         """
         Test when user has blocked notice, but notice ought to be there (NOOP)
         """
-        self._rlsn._auth_blocking.check_auth_blocking = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(None),
+        self._rlsn._auth_blocking.check_auth_blocking = AsyncMock(  # type: ignore[method-assign]
+            return_value=None,
             side_effect=ResourceLimitError(403, "foo"),
         )
 
         mock_event = Mock(
             type=EventTypes.Message, content={"msgtype": ServerNoticeMsgType}
         )
-        self._rlsn._store.get_events = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable({"123": mock_event})
+        self._rlsn._store.get_events = AsyncMock(  # type: ignore[method-assign]
+            return_value={"123": mock_event}
         )
 
         self.get_success(self._rlsn.maybe_send_server_notice_to_user(self.user_id))
@@ -145,8 +142,8 @@ class TestResourceLimitsServerNotices(unittest.HomeserverTestCase):
         """
         Test when user does not have blocked notice, but should have one
         """
-        self._rlsn._auth_blocking.check_auth_blocking = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(None),
+        self._rlsn._auth_blocking.check_auth_blocking = AsyncMock(  # type: ignore[method-assign]
+            return_value=None,
             side_effect=ResourceLimitError(403, "foo"),
         )
         self.get_success(self._rlsn.maybe_send_server_notice_to_user(self.user_id))
@@ -158,8 +155,8 @@ class TestResourceLimitsServerNotices(unittest.HomeserverTestCase):
         """
         Test when user does not have blocked notice, nor should they (NOOP)
         """
-        self._rlsn._auth_blocking.check_auth_blocking = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(None)
+        self._rlsn._auth_blocking.check_auth_blocking = AsyncMock(  # type: ignore[method-assign]
+            return_value=None
         )
 
         self.get_success(self._rlsn.maybe_send_server_notice_to_user(self.user_id))
@@ -171,12 +168,10 @@ class TestResourceLimitsServerNotices(unittest.HomeserverTestCase):
         Test when user is not part of the MAU cohort - this should not ever
         happen - but ...
         """
-        self._rlsn._auth_blocking.check_auth_blocking = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(None)
-        )
-        self._rlsn._store.user_last_seen_monthly_active = Mock(
-            return_value=make_awaitable(None)
+        self._rlsn._auth_blocking.check_auth_blocking = AsyncMock(  # type: ignore[method-assign]
+            return_value=None
         )
+        self._rlsn._store.user_last_seen_monthly_active = AsyncMock(return_value=None)
         self.get_success(self._rlsn.maybe_send_server_notice_to_user(self.user_id))
 
         self._send_notice.assert_not_called()
@@ -189,8 +184,8 @@ class TestResourceLimitsServerNotices(unittest.HomeserverTestCase):
         Test that when server is over MAU limit and alerting is suppressed, then
         an alert message is not sent into the room
         """
-        self._rlsn._auth_blocking.check_auth_blocking = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(None),
+        self._rlsn._auth_blocking.check_auth_blocking = AsyncMock(  # type: ignore[method-assign]
+            return_value=None,
             side_effect=ResourceLimitError(
                 403, "foo", limit_type=LimitBlockingTypes.MONTHLY_ACTIVE_USER
             ),
@@ -204,8 +199,8 @@ class TestResourceLimitsServerNotices(unittest.HomeserverTestCase):
         """
         Test that when a server is disabled, that MAU limit alerting is ignored.
         """
-        self._rlsn._auth_blocking.check_auth_blocking = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(None),
+        self._rlsn._auth_blocking.check_auth_blocking = AsyncMock(  # type: ignore[method-assign]
+            return_value=None,
             side_effect=ResourceLimitError(
                 403, "foo", limit_type=LimitBlockingTypes.HS_DISABLED
             ),
@@ -223,22 +218,22 @@ class TestResourceLimitsServerNotices(unittest.HomeserverTestCase):
         When the room is already in a blocked state, test that when alerting
         is suppressed that the room is returned to an unblocked state.
         """
-        self._rlsn._auth_blocking.check_auth_blocking = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(None),
+        self._rlsn._auth_blocking.check_auth_blocking = AsyncMock(  # type: ignore[method-assign]
+            return_value=None,
             side_effect=ResourceLimitError(
                 403, "foo", limit_type=LimitBlockingTypes.MONTHLY_ACTIVE_USER
             ),
         )
 
-        self._rlsn._is_room_currently_blocked = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable((True, []))
+        self._rlsn._is_room_currently_blocked = AsyncMock(  # type: ignore[method-assign]
+            return_value=(True, [])
         )
 
         mock_event = Mock(
             type=EventTypes.Message, content={"msgtype": ServerNoticeMsgType}
         )
-        self._rlsn._store.get_events = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable({"123": mock_event})
+        self._rlsn._store.get_events = AsyncMock(  # type: ignore[method-assign]
+            return_value={"123": mock_event}
         )
         self.get_success(self._rlsn.maybe_send_server_notice_to_user(self.user_id))
 
@@ -284,11 +279,9 @@ class TestResourceLimitsServerNoticesWithRealRooms(unittest.HomeserverTestCase):
         self.user_id = "@user_id:test"
 
     def test_server_notice_only_sent_once(self) -> None:
-        self.store.get_monthly_active_count = Mock(return_value=make_awaitable(1000))
+        self.store.get_monthly_active_count = AsyncMock(return_value=1000)
 
-        self.store.user_last_seen_monthly_active = Mock(
-            return_value=make_awaitable(1000)
-        )
+        self.store.user_last_seen_monthly_active = AsyncMock(return_value=1000)
 
         # Call the function multiple times to ensure we only send the notice once
         self.get_success(self._rlsn.maybe_send_server_notice_to_user(self.user_id))
@@ -327,7 +320,7 @@ class TestResourceLimitsServerNoticesWithRealRooms(unittest.HomeserverTestCase):
         hasn't been reached (since it's the only user and the limit is 5), so users
         shouldn't receive a server notice.
         """
-        m = Mock(return_value=make_awaitable(None))
+        m = AsyncMock(return_value=None)
         self._rlsn._server_notices_manager.maybe_get_notice_room_for_user = m
 
         user_id = self.register_user("user", "password")
diff --git a/tests/storage/databases/main/test_lock.py b/tests/storage/databases/main/test_lock.py
index f541f1d6be..650b4941ba 100644
--- a/tests/storage/databases/main/test_lock.py
+++ b/tests/storage/databases/main/test_lock.py
@@ -132,6 +132,7 @@ class LockTestCase(unittest.HomeserverTestCase):
 
         # We simulate the process getting stuck by cancelling the looping call
         # that keeps the lock active.
+        assert lock._looping_call
         lock._looping_call.stop()
 
         # Wait for the lock to timeout.
@@ -403,6 +404,7 @@ class ReadWriteLockTestCase(unittest.HomeserverTestCase):
 
         # We simulate the process getting stuck by cancelling the looping call
         # that keeps the lock active.
+        assert lock._looping_call
         lock._looping_call.stop()
 
         # Wait for the lock to timeout.
diff --git a/tests/storage/test_appservice.py b/tests/storage/test_appservice.py
index 71302facd1..cbce26a725 100644
--- a/tests/storage/test_appservice.py
+++ b/tests/storage/test_appservice.py
@@ -15,7 +15,7 @@ import json
 import os
 import tempfile
 from typing import List, cast
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 import yaml
 
@@ -35,7 +35,6 @@ from synapse.types import DeviceListUpdates
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 
 
 class ApplicationServiceStoreTestCase(unittest.HomeserverTestCase):
@@ -339,7 +338,7 @@ class ApplicationServiceTransactionStoreTestCase(unittest.HomeserverTestCase):
 
         # we aren't testing store._base stuff here, so mock this out
         # (ignore needed because Mypy won't allow us to assign to a method otherwise)
-        self.store.get_events_as_list = Mock(return_value=make_awaitable(events))  # type: ignore[assignment]
+        self.store.get_events_as_list = AsyncMock(return_value=events)  # type: ignore[method-assign]
 
         self.get_success(self._insert_txn(self.as_list[1]["id"], 9, other_events))
         self.get_success(self._insert_txn(service.id, 10, events))
diff --git a/tests/storage/test_background_update.py b/tests/storage/test_background_update.py
index a4a823a252..abf7d0564d 100644
--- a/tests/storage/test_background_update.py
+++ b/tests/storage/test_background_update.py
@@ -11,8 +11,8 @@
 # WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
 # See the License for the specific language governing permissions and
 # limitations under the License.
-
-from unittest.mock import Mock
+import logging
+from unittest.mock import AsyncMock, Mock
 
 import yaml
 
@@ -32,7 +32,6 @@ from synapse.types import JsonDict
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import make_awaitable, simple_async_mock
 from tests.unittest import override_config
 
 
@@ -331,6 +330,28 @@ class BackgroundUpdateTestCase(unittest.HomeserverTestCase):
         self.update_handler.side_effect = update_short
         self.get_success(self.updates.do_next_background_update(False))
 
+    def test_failed_update_logs_exception_details(self) -> None:
+        needle = "RUH ROH RAGGY"
+
+        def failing_update(progress: JsonDict, count: int) -> int:
+            raise Exception(needle)
+
+        self.update_handler.side_effect = failing_update
+        self.update_handler.reset_mock()
+
+        self.get_success(
+            self.store.db_pool.simple_insert(
+                "background_updates",
+                values={"update_name": "test_update", "progress_json": "{}"},
+            )
+        )
+
+        with self.assertLogs(level=logging.ERROR) as logs:
+            # Expect a back-to-back RuntimeError to be raised
+            self.get_failure(self.updates.run_background_updates(False), RuntimeError)
+
+        self.assertTrue(any(needle in log for log in logs.output), logs.output)
+
 
 class BackgroundUpdateControllerTestCase(unittest.HomeserverTestCase):
     def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
@@ -348,8 +369,8 @@ class BackgroundUpdateControllerTestCase(unittest.HomeserverTestCase):
 
         # Mock out the AsyncContextManager
         class MockCM:
-            __aenter__ = simple_async_mock(return_value=None)
-            __aexit__ = simple_async_mock(return_value=None)
+            __aenter__ = AsyncMock(return_value=None)
+            __aexit__ = AsyncMock(return_value=None)
 
         self._update_ctx_manager = MockCM
 
@@ -363,9 +384,9 @@ class BackgroundUpdateControllerTestCase(unittest.HomeserverTestCase):
         # Register the callbacks with more mocks
         self.hs.get_module_api().register_background_update_controller_callbacks(
             on_update=self._on_update,
-            min_batch_size=Mock(return_value=make_awaitable(self._default_batch_size)),
-            default_batch_size=Mock(
-                return_value=make_awaitable(self._default_batch_size),
+            min_batch_size=AsyncMock(return_value=self._default_batch_size),
+            default_batch_size=AsyncMock(
+                return_value=self._default_batch_size,
             ),
         )
 
diff --git a/tests/storage/test_client_ips.py b/tests/storage/test_client_ips.py
index 209d68b40b..6b9692c486 100644
--- a/tests/storage/test_client_ips.py
+++ b/tests/storage/test_client_ips.py
@@ -14,7 +14,7 @@
 # limitations under the License.
 
 from typing import Any, Dict
-from unittest.mock import Mock
+from unittest.mock import AsyncMock
 
 from parameterized import parameterized
 
@@ -30,7 +30,6 @@ from synapse.util import Clock
 
 from tests import unittest
 from tests.server import make_request
-from tests.test_utils import make_awaitable
 from tests.unittest import override_config
 
 
@@ -66,15 +65,15 @@ class ClientIpStoreTestCase(unittest.HomeserverTestCase):
         )
 
         r = result[(user_id, device_id)]
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "user_id": user_id,
                 "device_id": device_id,
                 "ip": "ip",
                 "user_agent": "user_agent",
                 "last_seen": 12345678000,
-            },
-            r,
+            }.items(),
+            r.items(),
         )
 
     def test_insert_new_client_ip_none_device_id(self) -> None:
@@ -443,9 +442,7 @@ class ClientIpStoreTestCase(unittest.HomeserverTestCase):
         lots_of_users = 100
         user_id = "@user:server"
 
-        self.store.get_monthly_active_count = Mock(
-            return_value=make_awaitable(lots_of_users)
-        )
+        self.store.get_monthly_active_count = AsyncMock(return_value=lots_of_users)
         self.get_success(
             self.store.insert_client_ip(
                 user_id, "access_token", "ip", "user_agent", "device_id"
@@ -529,15 +526,15 @@ class ClientIpStoreTestCase(unittest.HomeserverTestCase):
         )
 
         r = result[(user_id, device_id)]
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "user_id": user_id,
                 "device_id": device_id,
                 "ip": None,
                 "user_agent": None,
                 "last_seen": None,
-            },
-            r,
+            }.items(),
+            r.items(),
         )
 
         # Register the background update to run again.
@@ -564,15 +561,15 @@ class ClientIpStoreTestCase(unittest.HomeserverTestCase):
         )
 
         r = result[(user_id, device_id)]
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "user_id": user_id,
                 "device_id": device_id,
                 "ip": "ip",
                 "user_agent": "user_agent",
                 "last_seen": 0,
-            },
-            r,
+            }.items(),
+            r.items(),
         )
 
     def test_old_user_ips_pruned(self) -> None:
@@ -643,15 +640,15 @@ class ClientIpStoreTestCase(unittest.HomeserverTestCase):
         )
 
         r = result2[(user_id, device_id)]
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "user_id": user_id,
                 "device_id": device_id,
                 "ip": "ip",
                 "user_agent": "user_agent",
                 "last_seen": 0,
-            },
-            r,
+            }.items(),
+            r.items(),
         )
 
     def test_invalid_user_agents_are_ignored(self) -> None:
@@ -780,13 +777,13 @@ class ClientIpAuthTestCase(unittest.HomeserverTestCase):
             self.store.get_last_client_ip_by_device(self.user_id, device_id)
         )
         r = result[(self.user_id, device_id)]
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "user_id": self.user_id,
                 "device_id": device_id,
                 "ip": expected_ip,
                 "user_agent": "Mozzila pizza",
                 "last_seen": 123456100,
-            },
-            r,
+            }.items(),
+            r.items(),
         )
diff --git a/tests/storage/test_devices.py b/tests/storage/test_devices.py
index f03807c8f9..58ab41cf26 100644
--- a/tests/storage/test_devices.py
+++ b/tests/storage/test_devices.py
@@ -58,13 +58,13 @@ class DeviceStoreTestCase(HomeserverTestCase):
 
         res = self.get_success(self.store.get_device("user_id", "device_id"))
         assert res is not None
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "user_id": "user_id",
                 "device_id": "device_id",
                 "display_name": "display_name",
-            },
-            res,
+            }.items(),
+            res.items(),
         )
 
     def test_get_devices_by_user(self) -> None:
@@ -80,21 +80,21 @@ class DeviceStoreTestCase(HomeserverTestCase):
 
         res = self.get_success(self.store.get_devices_by_user("user_id"))
         self.assertEqual(2, len(res.keys()))
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "user_id": "user_id",
                 "device_id": "device1",
                 "display_name": "display_name 1",
-            },
-            res["device1"],
+            }.items(),
+            res["device1"].items(),
         )
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "user_id": "user_id",
                 "device_id": "device2",
                 "display_name": "display_name 2",
-            },
-            res["device2"],
+            }.items(),
+            res["device2"].items(),
         )
 
     def test_count_devices_by_users(self) -> None:
diff --git a/tests/storage/test_end_to_end_keys.py b/tests/storage/test_end_to_end_keys.py
index 5fde3b9c78..2033377b52 100644
--- a/tests/storage/test_end_to_end_keys.py
+++ b/tests/storage/test_end_to_end_keys.py
@@ -38,7 +38,7 @@ class EndToEndKeyStoreTestCase(HomeserverTestCase):
         self.assertIn("user", res)
         self.assertIn("device", res["user"])
         dev = res["user"]["device"]
-        self.assertDictContainsSubset(json, dev)
+        self.assertLessEqual(json.items(), dev.items())
 
     def test_reupload_key(self) -> None:
         now = 1470174257070
@@ -71,8 +71,12 @@ class EndToEndKeyStoreTestCase(HomeserverTestCase):
         self.assertIn("user", res)
         self.assertIn("device", res["user"])
         dev = res["user"]["device"]
-        self.assertDictContainsSubset(
-            {"key": "value", "unsigned": {"device_display_name": "display_name"}}, dev
+        self.assertLessEqual(
+            {
+                "key": "value",
+                "unsigned": {"device_display_name": "display_name"},
+            }.items(),
+            dev.items(),
         )
 
     def test_multiple_devices(self) -> None:
diff --git a/tests/storage/test_monthly_active_users.py b/tests/storage/test_monthly_active_users.py
index 2827738379..49366440ce 100644
--- a/tests/storage/test_monthly_active_users.py
+++ b/tests/storage/test_monthly_active_users.py
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 from typing import Any, Dict, List
-from unittest.mock import Mock
+from unittest.mock import AsyncMock
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -21,7 +21,6 @@ from synapse.server import HomeServer
 from synapse.util import Clock
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 from tests.unittest import default_config, override_config
 
 FORTY_DAYS = 40 * 24 * 60 * 60
@@ -253,7 +252,7 @@ class MonthlyActiveUsersTestCase(unittest.HomeserverTestCase):
         )
         self.get_success(d)
 
-        self.store.upsert_monthly_active_user = Mock(return_value=make_awaitable(None))  # type: ignore[assignment]
+        self.store.upsert_monthly_active_user = AsyncMock(return_value=None)  # type: ignore[method-assign]
 
         d = self.store.populate_monthly_active_users(user_id)
         self.get_success(d)
@@ -261,24 +260,22 @@ class MonthlyActiveUsersTestCase(unittest.HomeserverTestCase):
         self.store.upsert_monthly_active_user.assert_not_called()
 
     def test_populate_monthly_users_should_update(self) -> None:
-        self.store.upsert_monthly_active_user = Mock(return_value=make_awaitable(None))  # type: ignore[assignment]
+        self.store.upsert_monthly_active_user = AsyncMock(return_value=None)  # type: ignore[method-assign]
 
-        self.store.is_trial_user = Mock(return_value=make_awaitable(False))  # type: ignore[assignment]
+        self.store.is_trial_user = AsyncMock(return_value=False)  # type: ignore[method-assign]
 
-        self.store.user_last_seen_monthly_active = Mock(
-            return_value=make_awaitable(None)
-        )
+        self.store.user_last_seen_monthly_active = AsyncMock(return_value=None)
         d = self.store.populate_monthly_active_users("user_id")
         self.get_success(d)
 
         self.store.upsert_monthly_active_user.assert_called_once()
 
     def test_populate_monthly_users_should_not_update(self) -> None:
-        self.store.upsert_monthly_active_user = Mock(return_value=make_awaitable(None))  # type: ignore[assignment]
+        self.store.upsert_monthly_active_user = AsyncMock(return_value=None)  # type: ignore[method-assign]
 
-        self.store.is_trial_user = Mock(return_value=make_awaitable(False))  # type: ignore[assignment]
-        self.store.user_last_seen_monthly_active = Mock(
-            return_value=make_awaitable(self.hs.get_clock().time_msec())
+        self.store.is_trial_user = AsyncMock(return_value=False)  # type: ignore[method-assign]
+        self.store.user_last_seen_monthly_active = AsyncMock(
+            return_value=self.hs.get_clock().time_msec()
         )
 
         d = self.store.populate_monthly_active_users("user_id")
@@ -359,7 +356,7 @@ class MonthlyActiveUsersTestCase(unittest.HomeserverTestCase):
 
     @override_config({"limit_usage_by_mau": False, "mau_stats_only": False})
     def test_no_users_when_not_tracking(self) -> None:
-        self.store.upsert_monthly_active_user = Mock(return_value=make_awaitable(None))  # type: ignore[assignment]
+        self.store.upsert_monthly_active_user = AsyncMock(return_value=None)  # type: ignore[method-assign]
 
         self.get_success(self.store.populate_monthly_active_users("@user:sever"))
 
diff --git a/tests/storage/test_registration.py b/tests/storage/test_registration.py
index ba41459d08..95c9792d54 100644
--- a/tests/storage/test_registration.py
+++ b/tests/storage/test_registration.py
@@ -51,6 +51,7 @@ class RegistrationStoreTestCase(HomeserverTestCase):
                 "locked": 0,
                 "shadow_banned": 0,
                 "approved": 1,
+                "last_seen_ts": None,
             },
             (self.get_success(self.store.get_user_by_id(self.user_id))),
         )
diff --git a/tests/storage/test_room.py b/tests/storage/test_room.py
index 71ec74eadc..1e27f2c275 100644
--- a/tests/storage/test_room.py
+++ b/tests/storage/test_room.py
@@ -44,13 +44,13 @@ class RoomStoreTestCase(HomeserverTestCase):
     def test_get_room(self) -> None:
         res = self.get_success(self.store.get_room(self.room.to_string()))
         assert res is not None
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "room_id": self.room.to_string(),
                 "creator": self.u_creator.to_string(),
                 "is_public": True,
-            },
-            res,
+            }.items(),
+            res.items(),
         )
 
     def test_get_room_unknown_room(self) -> None:
@@ -59,13 +59,13 @@ class RoomStoreTestCase(HomeserverTestCase):
     def test_get_room_with_stats(self) -> None:
         res = self.get_success(self.store.get_room_with_stats(self.room.to_string()))
         assert res is not None
-        self.assertDictContainsSubset(
+        self.assertLessEqual(
             {
                 "room_id": self.room.to_string(),
                 "creator": self.u_creator.to_string(),
                 "public": True,
-            },
-            res,
+            }.items(),
+            res.items(),
         )
 
     def test_get_room_with_stats_unknown_room(self) -> None:
diff --git a/tests/storage/util/test_partial_state_events_tracker.py b/tests/storage/util/test_partial_state_events_tracker.py
index 0e3fc2a77f..29be8cdbd0 100644
--- a/tests/storage/util/test_partial_state_events_tracker.py
+++ b/tests/storage/util/test_partial_state_events_tracker.py
@@ -22,7 +22,6 @@ from synapse.storage.util.partial_state_events_tracker import (
     PartialStateEventsTracker,
 )
 
-from tests.test_utils import make_awaitable
 from tests.unittest import TestCase
 
 
@@ -124,16 +123,17 @@ class PartialStateEventsTrackerTestCase(TestCase):
 class PartialCurrentStateTrackerTestCase(TestCase):
     def setUp(self) -> None:
         self.mock_store = mock.Mock(spec_set=["is_partial_state_room"])
+        self.mock_store.is_partial_state_room = mock.AsyncMock()
 
         self.tracker = PartialCurrentStateTracker(self.mock_store)
 
     def test_does_not_block_for_full_state_rooms(self) -> None:
-        self.mock_store.is_partial_state_room.return_value = make_awaitable(False)
+        self.mock_store.is_partial_state_room.return_value = False
 
         self.successResultOf(ensureDeferred(self.tracker.await_full_state("room_id")))
 
     def test_blocks_for_partial_room_state(self) -> None:
-        self.mock_store.is_partial_state_room.return_value = make_awaitable(True)
+        self.mock_store.is_partial_state_room.return_value = True
 
         d = ensureDeferred(self.tracker.await_full_state("room_id"))
 
@@ -156,7 +156,7 @@ class PartialCurrentStateTrackerTestCase(TestCase):
         self.successResultOf(ensureDeferred(self.tracker.await_full_state("room_id")))
 
     def test_cancellation(self) -> None:
-        self.mock_store.is_partial_state_room.return_value = make_awaitable(True)
+        self.mock_store.is_partial_state_room.return_value = True
 
         d1 = ensureDeferred(self.tracker.await_full_state("room_id"))
         self.assertNoResult(d1)
diff --git a/tests/test_federation.py b/tests/test_federation.py
index 6d15ac7597..f8ade6da38 100644
--- a/tests/test_federation.py
+++ b/tests/test_federation.py
@@ -13,7 +13,7 @@
 # limitations under the License.
 
 from typing import Collection, List, Optional, Union
-from unittest.mock import Mock
+from unittest.mock import AsyncMock, Mock
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -31,7 +31,6 @@ from synapse.util import Clock
 from synapse.util.retryutils import NotRetryingDestination
 
 from tests import unittest
-from tests.test_utils import make_awaitable
 
 
 class MessageAcceptTests(unittest.HomeserverTestCase):
@@ -81,7 +80,7 @@ class MessageAcceptTests(unittest.HomeserverTestCase):
         ) -> None:
             pass
 
-        federation_event_handler._check_event_auth = _check_event_auth  # type: ignore[assignment]
+        federation_event_handler._check_event_auth = _check_event_auth  # type: ignore[method-assign]
         self.client = self.hs.get_federation_client()
 
         async def _check_sigs_and_hash_for_pulled_events_and_fetch(
@@ -191,12 +190,12 @@ class MessageAcceptTests(unittest.HomeserverTestCase):
 
         # Register the mock on the federation client.
         federation_client = self.hs.get_federation_client()
-        federation_client.query_user_devices = Mock(side_effect=query_user_devices)  # type: ignore[assignment]
+        federation_client.query_user_devices = Mock(side_effect=query_user_devices)  # type: ignore[method-assign]
 
         # Register a mock on the store so that the incoming update doesn't fail because
         # we don't share a room with the user.
         store = self.hs.get_datastores().main
-        store.get_rooms_for_user = Mock(return_value=make_awaitable(["!someroom:test"]))
+        store.get_rooms_for_user = AsyncMock(return_value=["!someroom:test"])
 
         # Manually inject a fake device list update. We need this update to include at
         # least one prev_id so that the user's device list will need to be retried.
@@ -241,27 +240,24 @@ class MessageAcceptTests(unittest.HomeserverTestCase):
 
         # Register mock device list retrieval on the federation client.
         federation_client = self.hs.get_federation_client()
-        federation_client.query_user_devices = Mock(  # type: ignore[assignment]
-            return_value=make_awaitable(
-                {
+        federation_client.query_user_devices = AsyncMock(  # type: ignore[method-assign]
+            return_value={
+                "user_id": remote_user_id,
+                "stream_id": 1,
+                "devices": [],
+                "master_key": {
                     "user_id": remote_user_id,
-                    "stream_id": 1,
-                    "devices": [],
-                    "master_key": {
-                        "user_id": remote_user_id,
-                        "usage": ["master"],
-                        "keys": {"ed25519:" + remote_master_key: remote_master_key},
+                    "usage": ["master"],
+                    "keys": {"ed25519:" + remote_master_key: remote_master_key},
+                },
+                "self_signing_key": {
+                    "user_id": remote_user_id,
+                    "usage": ["self_signing"],
+                    "keys": {
+                        "ed25519:" + remote_self_signing_key: remote_self_signing_key
                     },
-                    "self_signing_key": {
-                        "user_id": remote_user_id,
-                        "usage": ["self_signing"],
-                        "keys": {
-                            "ed25519:"
-                            + remote_self_signing_key: remote_self_signing_key
-                        },
-                    },
-                }
-            )
+                },
+            }
         )
 
         # Resync the device list.
diff --git a/tests/test_state.py b/tests/test_state.py
index eded38c766..9c8679cc1d 100644
--- a/tests/test_state.py
+++ b/tests/test_state.py
@@ -714,7 +714,7 @@ class StateTestCase(unittest.TestCase):
         store = _DummyStore()
         store.register_events(old_state_1)
         store.register_events(old_state_2)
-        self.dummy_store.get_events = store.get_events  # type: ignore[assignment]
+        self.dummy_store.get_events = store.get_events  # type: ignore[method-assign]
 
         context: EventContext
         context = yield self._get_context(
@@ -773,7 +773,7 @@ class StateTestCase(unittest.TestCase):
         store = _DummyStore()
         store.register_events(old_state_1)
         store.register_events(old_state_2)
-        self.dummy_store.get_events = store.get_events  # type: ignore[assignment]
+        self.dummy_store.get_events = store.get_events  # type: ignore[method-assign]
 
         context: EventContext
         context = yield self._get_context(
diff --git a/tests/test_terms_auth.py b/tests/test_terms_auth.py
index 52424aa087..64a49488c6 100644
--- a/tests/test_terms_auth.py
+++ b/tests/test_terms_auth.py
@@ -85,7 +85,9 @@ class TermsTestCase(unittest.HomeserverTestCase):
             }
         }
         self.assertIsInstance(channel.json_body["params"], dict)
-        self.assertDictContainsSubset(channel.json_body["params"], expected_params)
+        self.assertLessEqual(
+            channel.json_body["params"].items(), expected_params.items()
+        )
 
         # We have to complete the dummy auth stage before completing the terms stage
         request_data = {
diff --git a/tests/test_utils/__init__.py b/tests/test_utils/__init__.py
index c8cc841d95..fa731426cd 100644
--- a/tests/test_utils/__init__.py
+++ b/tests/test_utils/__init__.py
@@ -18,10 +18,8 @@ Utilities for running the unit tests
 import json
 import sys
 import warnings
-from asyncio import Future
 from binascii import unhexlify
-from typing import TYPE_CHECKING, Any, Awaitable, Callable, Optional, Tuple, TypeVar
-from unittest.mock import Mock
+from typing import TYPE_CHECKING, Awaitable, Callable, Tuple, TypeVar
 
 import attr
 import zope.interface
@@ -57,27 +55,12 @@ def get_awaitable_result(awaitable: Awaitable[TV]) -> TV:
     raise Exception("awaitable has not yet completed")
 
 
-def make_awaitable(result: TV) -> Awaitable[TV]:
-    """
-    Makes an awaitable, suitable for mocking an `async` function.
-    This uses Futures as they can be awaited multiple times so can be returned
-    to multiple callers.
-    """
-    future: Future[TV] = Future()
-    future.set_result(result)
-    return future
-
-
 def setup_awaitable_errors() -> Callable[[], None]:
     """
     Convert warnings from a non-awaited coroutines into errors.
     """
     warnings.simplefilter("error", RuntimeWarning)
 
-    # unraisablehook was added in Python 3.8.
-    if not hasattr(sys, "unraisablehook"):
-        return lambda: None
-
     # State shared between unraisablehook and check_for_unraisable_exceptions.
     unraisable_exceptions = []
     orig_unraisablehook = sys.unraisablehook
@@ -100,18 +83,6 @@ def setup_awaitable_errors() -> Callable[[], None]:
     return cleanup
 
 
-def simple_async_mock(
-    return_value: Optional[TV] = None, raises: Optional[Exception] = None
-) -> Mock:
-    # AsyncMock is not available in python3.5, this mimics part of its behaviour
-    async def cb(*args: Any, **kwargs: Any) -> Optional[TV]:
-        if raises:
-            raise raises
-        return return_value
-
-    return Mock(side_effect=cb)
-
-
 # Type ignore: it does not fully implement IResponse, but is good enough for tests
 @zope.interface.implementer(IResponse)
 @attr.s(slots=True, frozen=True, auto_attribs=True)
diff --git a/tests/unittest.py b/tests/unittest.py
index b0721e060c..5d3640d8ac 100644
--- a/tests/unittest.py
+++ b/tests/unittest.py
@@ -313,7 +313,7 @@ class HomeserverTestCase(TestCase):
         servlets: List of servlet registration function.
         user_id (str): The user ID to assume if auth is hijacked.
         hijack_auth: Whether to hijack auth to return the user specified
-        in user_id.
+           in user_id.
     """
 
     hijack_auth: ClassVar[bool] = True
@@ -395,9 +395,9 @@ class HomeserverTestCase(TestCase):
                     )
 
                 # Type ignore: mypy doesn't like us assigning to methods.
-                self.hs.get_auth().get_user_by_req = get_requester  # type: ignore[assignment]
-                self.hs.get_auth().get_user_by_access_token = get_requester  # type: ignore[assignment]
-                self.hs.get_auth().get_access_token_from_request = Mock(return_value=token)  # type: ignore[assignment]
+                self.hs.get_auth().get_user_by_req = get_requester  # type: ignore[method-assign]
+                self.hs.get_auth().get_user_by_access_token = get_requester  # type: ignore[method-assign]
+                self.hs.get_auth().get_access_token_from_request = Mock(return_value=token)  # type: ignore[method-assign]
 
         if self.needs_threadpool:
             self.reactor.threadpool = ThreadPool()  # type: ignore[assignment]
diff --git a/tests/util/test_async_helpers.py b/tests/util/test_async_helpers.py
index 91cac9822a..05983ed434 100644
--- a/tests/util/test_async_helpers.py
+++ b/tests/util/test_async_helpers.py
@@ -60,11 +60,9 @@ class ObservableDeferredTest(TestCase):
         observer1.addBoth(check_called_first)
 
         # store the results
-        results: List[Optional[ObservableDeferred[int]]] = [None, None]
+        results: List[Optional[int]] = [None, None]
 
-        def check_val(
-            res: ObservableDeferred[int], idx: int
-        ) -> ObservableDeferred[int]:
+        def check_val(res: int, idx: int) -> int:
             results[idx] = res
             return res
 
@@ -93,14 +91,14 @@ class ObservableDeferredTest(TestCase):
         observer1.addBoth(check_called_first)
 
         # store the results
-        results: List[Optional[ObservableDeferred[str]]] = [None, None]
+        results: List[Optional[Failure]] = [None, None]
 
-        def check_val(res: ObservableDeferred[str], idx: int) -> None:
+        def check_failure(res: Failure, idx: int) -> None:
             results[idx] = res
             return None
 
-        observer1.addErrback(check_val, 0)
-        observer2.addErrback(check_val, 1)
+        observer1.addErrback(check_failure, 0)
+        observer2.addErrback(check_failure, 1)
 
         try:
             raise Exception("gah!")
diff --git a/tests/util/test_task_scheduler.py b/tests/util/test_task_scheduler.py
index 3a97559bf0..8665aeb50c 100644
--- a/tests/util/test_task_scheduler.py
+++ b/tests/util/test_task_scheduler.py
@@ -22,10 +22,11 @@ from synapse.types import JsonMapping, ScheduledTask, TaskStatus
 from synapse.util import Clock
 from synapse.util.task_scheduler import TaskScheduler
 
-from tests import unittest
+from tests.replication._base import BaseMultiWorkerStreamTestCase
+from tests.unittest import HomeserverTestCase, override_config
 
 
-class TestTaskScheduler(unittest.HomeserverTestCase):
+class TestTaskScheduler(HomeserverTestCase):
     def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
         self.task_scheduler = hs.get_task_scheduler()
         self.task_scheduler.register_action(self._test_task, "_test_task")
@@ -34,7 +35,7 @@ class TestTaskScheduler(unittest.HomeserverTestCase):
         self.task_scheduler.register_action(self._resumable_task, "_resumable_task")
 
     async def _test_task(
-        self, task: ScheduledTask, first_launch: bool
+        self, task: ScheduledTask
     ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
         # This test task will copy the parameters to the result
         result = None
@@ -77,7 +78,7 @@ class TestTaskScheduler(unittest.HomeserverTestCase):
         self.assertIsNone(task)
 
     async def _sleeping_task(
-        self, task: ScheduledTask, first_launch: bool
+        self, task: ScheduledTask
     ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
         # Sleep for a second
         await deferLater(self.reactor, 1, lambda: None)
@@ -85,24 +86,18 @@ class TestTaskScheduler(unittest.HomeserverTestCase):
 
     def test_schedule_lot_of_tasks(self) -> None:
         """Schedule more than `TaskScheduler.MAX_CONCURRENT_RUNNING_TASKS` tasks and check the behavior."""
-        timestamp = self.clock.time_msec() + 30 * 1000
         task_ids = []
         for i in range(TaskScheduler.MAX_CONCURRENT_RUNNING_TASKS + 1):
             task_ids.append(
                 self.get_success(
                     self.task_scheduler.schedule_task(
                         "_sleeping_task",
-                        timestamp=timestamp,
                         params={"val": i},
                     )
                 )
             )
 
-        # The timestamp being 30s after now the task should been executed
-        # after the first scheduling loop is run
-        self.reactor.advance((TaskScheduler.SCHEDULE_INTERVAL_MS / 1000))
-
-        # This is to give the time to the sleeping tasks to finish
+        # This is to give the time to the active tasks to finish
         self.reactor.advance(1)
 
         # Check that only MAX_CONCURRENT_RUNNING_TASKS tasks has run and that one
@@ -120,10 +115,11 @@ class TestTaskScheduler(unittest.HomeserverTestCase):
         )
 
         scheduled_tasks = [
-            t for t in tasks if t is not None and t.status == TaskStatus.SCHEDULED
+            t for t in tasks if t is not None and t.status == TaskStatus.ACTIVE
         ]
         self.assertEquals(len(scheduled_tasks), 1)
 
+        # We need to wait for the next run of the scheduler loop
         self.reactor.advance((TaskScheduler.SCHEDULE_INTERVAL_MS / 1000))
         self.reactor.advance(1)
 
@@ -138,7 +134,7 @@ class TestTaskScheduler(unittest.HomeserverTestCase):
         )
 
     async def _raising_task(
-        self, task: ScheduledTask, first_launch: bool
+        self, task: ScheduledTask
     ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
         raise Exception("raising")
 
@@ -146,15 +142,13 @@ class TestTaskScheduler(unittest.HomeserverTestCase):
         """Schedule a task raising an exception and check it runs to failure and report exception content."""
         task_id = self.get_success(self.task_scheduler.schedule_task("_raising_task"))
 
-        self.reactor.advance((TaskScheduler.SCHEDULE_INTERVAL_MS / 1000))
-
         task = self.get_success(self.task_scheduler.get_task(task_id))
         assert task is not None
         self.assertEqual(task.status, TaskStatus.FAILED)
         self.assertEqual(task.error, "raising")
 
     async def _resumable_task(
-        self, task: ScheduledTask, first_launch: bool
+        self, task: ScheduledTask
     ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
         if task.result and "in_progress" in task.result:
             return TaskStatus.COMPLETE, {"success": True}, None
@@ -169,8 +163,6 @@ class TestTaskScheduler(unittest.HomeserverTestCase):
         """Schedule a resumable task and check that it gets properly resumed and complete after simulating a synapse restart."""
         task_id = self.get_success(self.task_scheduler.schedule_task("_resumable_task"))
 
-        self.reactor.advance((TaskScheduler.SCHEDULE_INTERVAL_MS / 1000))
-
         task = self.get_success(self.task_scheduler.get_task(task_id))
         assert task is not None
         self.assertEqual(task.status, TaskStatus.ACTIVE)
@@ -184,3 +176,33 @@ class TestTaskScheduler(unittest.HomeserverTestCase):
         self.assertEqual(task.status, TaskStatus.COMPLETE)
         assert task.result is not None
         self.assertTrue(task.result.get("success"))
+
+
+class TestTaskSchedulerWithBackgroundWorker(BaseMultiWorkerStreamTestCase):
+    def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
+        self.task_scheduler = hs.get_task_scheduler()
+        self.task_scheduler.register_action(self._test_task, "_test_task")
+
+    async def _test_task(
+        self, task: ScheduledTask
+    ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
+        return (TaskStatus.COMPLETE, None, None)
+
+    @override_config({"run_background_tasks_on": "worker1"})
+    def test_schedule_task(self) -> None:
+        """Check that a task scheduled to run now is launch right away on the background worker."""
+        bg_worker_hs = self.make_worker_hs(
+            "synapse.app.generic_worker",
+            extra_config={"worker_name": "worker1"},
+        )
+        bg_worker_hs.get_task_scheduler().register_action(self._test_task, "_test_task")
+
+        task_id = self.get_success(
+            self.task_scheduler.schedule_task(
+                "_test_task",
+            )
+        )
+
+        task = self.get_success(self.task_scheduler.get_task(task_id))
+        assert task is not None
+        self.assertEqual(task.status, TaskStatus.COMPLETE)