diff --git a/CHANGES.md b/CHANGES.md
index a41abbefba..93efa3ce56 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -1,3 +1,19 @@
+Synapse 1.33.2 (2021-05-11)
+===========================
+
+Due to the security issue highlighted below, server administrators are encouraged to update Synapse. We are not aware of these vulnerabilities being exploited in the wild.
+
+Security advisory
+-----------------
+
+This release fixes a denial of service attack ([CVE-2021-29471](https://github.com/matrix-org/synapse/security/advisories/GHSA-x345-32rc-8h85)) against Synapse's push rules implementation. Server admins are encouraged to upgrade.
+
+Internal Changes
+----------------
+
+- Unpin attrs dependency. ([\#9946](https://github.com/matrix-org/synapse/issues/9946))
+
+
 Synapse 1.33.1 (2021-05-06)
 ===========================
 
diff --git a/changelog.d/9946.misc b/changelog.d/9946.misc
deleted file mode 100644
index 142ec5496f..0000000000
--- a/changelog.d/9946.misc
+++ /dev/null
@@ -1 +0,0 @@
-Unpin attrs dependency.
diff --git a/debian/changelog b/debian/changelog
index de50dd14ea..76b82c172e 100644
--- a/debian/changelog
+++ b/debian/changelog
@@ -1,3 +1,9 @@
+matrix-synapse-py3 (1.33.2) stable; urgency=medium
+
+  * New synapse release 1.33.2.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 11 May 2021 11:17:59 +0100
+
 matrix-synapse-py3 (1.33.1) stable; urgency=medium
 
   * New synapse release 1.33.1.
diff --git a/synapse/__init__.py b/synapse/__init__.py
index 441cd8b339..ce822ccb04 100644
--- a/synapse/__init__.py
+++ b/synapse/__init__.py
@@ -47,7 +47,7 @@ try:
 except ImportError:
     pass
 
-__version__ = "1.33.1"
+__version__ = "1.33.2"
 
 if bool(os.environ.get("SYNAPSE_TEST_PATCH_LOG_CONTEXTS", False)):
     # We import here so that we don't have to install a bunch of deps when
diff --git a/synapse/config/tls.py b/synapse/config/tls.py
index b041869758..7df4e4c3e6 100644
--- a/synapse/config/tls.py
+++ b/synapse/config/tls.py
@@ -17,7 +17,7 @@ import os
 import warnings
 from datetime import datetime
 from hashlib import sha256
-from typing import List, Optional
+from typing import List, Optional, Pattern
 
 from unpaddedbase64 import encode_base64
 
@@ -124,7 +124,7 @@ class TlsConfig(Config):
             fed_whitelist_entries = []
 
         # Support globs (*) in whitelist values
-        self.federation_certificate_verification_whitelist = []  # type: List[str]
+        self.federation_certificate_verification_whitelist = []  # type: List[Pattern]
         for entry in fed_whitelist_entries:
             try:
                 entry_regex = glob_to_regex(entry.encode("ascii").decode("ascii"))
diff --git a/synapse/push/push_rule_evaluator.py b/synapse/push/push_rule_evaluator.py
index 49ecb38522..98b90a4f51 100644
--- a/synapse/push/push_rule_evaluator.py
+++ b/synapse/push/push_rule_evaluator.py
@@ -19,6 +19,7 @@ from typing import Any, Dict, List, Optional, Pattern, Tuple, Union
 
 from synapse.events import EventBase
 from synapse.types import UserID
+from synapse.util import glob_to_regex, re_word_boundary
 from synapse.util.caches.lrucache import LruCache
 
 logger = logging.getLogger(__name__)
@@ -183,7 +184,7 @@ class PushRuleEvaluatorForEvent:
         r = regex_cache.get((display_name, False, True), None)
         if not r:
             r1 = re.escape(display_name)
-            r1 = _re_word_boundary(r1)
+            r1 = re_word_boundary(r1)
             r = re.compile(r1, flags=re.IGNORECASE)
             regex_cache[(display_name, False, True)] = r
 
@@ -212,7 +213,7 @@ def _glob_matches(glob: str, value: str, word_boundary: bool = False) -> bool:
     try:
         r = regex_cache.get((glob, True, word_boundary), None)
         if not r:
-            r = _glob_to_re(glob, word_boundary)
+            r = glob_to_regex(glob, word_boundary)
             regex_cache[(glob, True, word_boundary)] = r
         return bool(r.search(value))
     except re.error:
@@ -220,56 +221,6 @@ def _glob_matches(glob: str, value: str, word_boundary: bool = False) -> bool:
         return False
 
 
-def _glob_to_re(glob: str, word_boundary: bool) -> Pattern:
-    """Generates regex for a given glob.
-
-    Args:
-        glob
-        word_boundary: Whether to match against word boundaries or entire string.
-    """
-    if IS_GLOB.search(glob):
-        r = re.escape(glob)
-
-        r = r.replace(r"\*", ".*?")
-        r = r.replace(r"\?", ".")
-
-        # handle [abc], [a-z] and [!a-z] style ranges.
-        r = GLOB_REGEX.sub(
-            lambda x: (
-                "[%s%s]" % (x.group(1) and "^" or "", x.group(2).replace(r"\\\-", "-"))
-            ),
-            r,
-        )
-        if word_boundary:
-            r = _re_word_boundary(r)
-
-            return re.compile(r, flags=re.IGNORECASE)
-        else:
-            r = "^" + r + "$"
-
-            return re.compile(r, flags=re.IGNORECASE)
-    elif word_boundary:
-        r = re.escape(glob)
-        r = _re_word_boundary(r)
-
-        return re.compile(r, flags=re.IGNORECASE)
-    else:
-        r = "^" + re.escape(glob) + "$"
-        return re.compile(r, flags=re.IGNORECASE)
-
-
-def _re_word_boundary(r: str) -> str:
-    """
-    Adds word boundary characters to the start and end of an
-    expression to require that the match occur as a whole word,
-    but do so respecting the fact that strings starting or ending
-    with non-word characters will change word boundaries.
-    """
-    # we can't use \b as it chokes on unicode. however \W seems to be okay
-    # as shorthand for [^0-9A-Za-z_].
-    return r"(^|\W)%s(\W|$)" % (r,)
-
-
 def _flatten_dict(
     d: Union[EventBase, dict],
     prefix: Optional[List[str]] = None,
diff --git a/synapse/util/__init__.py b/synapse/util/__init__.py
index 0f84fa3f4e..b69f562ca5 100644
--- a/synapse/util/__init__.py
+++ b/synapse/util/__init__.py
@@ -15,6 +15,7 @@
 import json
 import logging
 import re
+from typing import Pattern
 
 import attr
 from frozendict import frozendict
@@ -26,6 +27,9 @@ from synapse.logging import context
 logger = logging.getLogger(__name__)
 
 
+_WILDCARD_RUN = re.compile(r"([\?\*]+)")
+
+
 def _reject_invalid_json(val):
     """Do not allow Infinity, -Infinity, or NaN values in JSON."""
     raise ValueError("Invalid JSON value: '%s'" % val)
@@ -158,25 +162,54 @@ def log_failure(failure, msg, consumeErrors=True):
         return failure
 
 
-def glob_to_regex(glob):
+def glob_to_regex(glob: str, word_boundary: bool = False) -> Pattern:
     """Converts a glob to a compiled regex object.
 
-    The regex is anchored at the beginning and end of the string.
-
     Args:
-        glob (str)
+        glob: pattern to match
+        word_boundary: If True, the pattern will be allowed to match at word boundaries
+           anywhere in the string. Otherwise, the pattern is anchored at the start and
+           end of the string.
 
     Returns:
-        re.RegexObject
+        compiled regex pattern
     """
-    res = ""
-    for c in glob:
-        if c == "*":
-            res = res + ".*"
-        elif c == "?":
-            res = res + "."
-        else:
-            res = res + re.escape(c)
 
-    # \A anchors at start of string, \Z at end of string
-    return re.compile(r"\A" + res + r"\Z", re.IGNORECASE)
+    # Patterns with wildcards must be simplified to avoid performance cliffs
+    # - The glob `?**?**?` is equivalent to the glob `???*`
+    # - The glob `???*` is equivalent to the regex `.{3,}`
+    chunks = []
+    for chunk in _WILDCARD_RUN.split(glob):
+        # No wildcards? re.escape()
+        if not _WILDCARD_RUN.match(chunk):
+            chunks.append(re.escape(chunk))
+            continue
+
+        # Wildcards? Simplify.
+        qmarks = chunk.count("?")
+        if "*" in chunk:
+            chunks.append(".{%d,}" % qmarks)
+        else:
+            chunks.append(".{%d}" % qmarks)
+
+    res = "".join(chunks)
+
+    if word_boundary:
+        res = re_word_boundary(res)
+    else:
+        # \A anchors at start of string, \Z at end of string
+        res = r"\A" + res + r"\Z"
+
+    return re.compile(res, re.IGNORECASE)
+
+
+def re_word_boundary(r: str) -> str:
+    """
+    Adds word boundary characters to the start and end of an
+    expression to require that the match occur as a whole word,
+    but do so respecting the fact that strings starting or ending
+    with non-word characters will change word boundaries.
+    """
+    # we can't use \b as it chokes on unicode. however \W seems to be okay
+    # as shorthand for [^0-9A-Za-z_].
+    return r"(^|\W)%s(\W|$)" % (r,)
diff --git a/tests/federation/test_federation_server.py b/tests/federation/test_federation_server.py
index 8508b6bd3b..1737891564 100644
--- a/tests/federation/test_federation_server.py
+++ b/tests/federation/test_federation_server.py
@@ -74,6 +74,25 @@ class ServerACLsTestCase(unittest.TestCase):
         self.assertFalse(server_matches_acl_event("[1:2::]", e))
         self.assertTrue(server_matches_acl_event("1:2:3:4", e))
 
+    def test_wildcard_matching(self):
+        e = _create_acl_event({"allow": ["good*.com"]})
+        self.assertTrue(
+            server_matches_acl_event("good.com", e),
+            "* matches 0 characters",
+        )
+        self.assertTrue(
+            server_matches_acl_event("GOOD.COM", e),
+            "pattern is case-insensitive",
+        )
+        self.assertTrue(
+            server_matches_acl_event("good.aa.com", e),
+            "* matches several characters, including '.'",
+        )
+        self.assertFalse(
+            server_matches_acl_event("ishgood.com", e),
+            "pattern does not allow prefixes",
+        )
+
 
 class StateQueryTests(unittest.FederatingHomeserverTestCase):
 
diff --git a/tests/push/test_push_rule_evaluator.py b/tests/push/test_push_rule_evaluator.py
index 45906ce720..a52e89e407 100644
--- a/tests/push/test_push_rule_evaluator.py
+++ b/tests/push/test_push_rule_evaluator.py
@@ -12,6 +12,8 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+from typing import Any, Dict
+
 from synapse.api.room_versions import RoomVersions
 from synapse.events import FrozenEvent
 from synapse.push import push_rule_evaluator
@@ -66,6 +68,170 @@ class PushRuleEvaluatorTestCase(unittest.TestCase):
         # A display name with spaces should work fine.
         self.assertTrue(evaluator.matches(condition, "@user:test", "foo bar"))
 
+    def _assert_matches(
+        self, condition: Dict[str, Any], content: Dict[str, Any], msg=None
+    ) -> None:
+        evaluator = self._get_evaluator(content)
+        self.assertTrue(evaluator.matches(condition, "@user:test", "display_name"), msg)
+
+    def _assert_not_matches(
+        self, condition: Dict[str, Any], content: Dict[str, Any], msg=None
+    ) -> None:
+        evaluator = self._get_evaluator(content)
+        self.assertFalse(
+            evaluator.matches(condition, "@user:test", "display_name"), msg
+        )
+
+    def test_event_match_body(self):
+        """Check that event_match conditions on content.body work as expected"""
+
+        # if the key is `content.body`, the pattern matches substrings.
+
+        # non-wildcards should match
+        condition = {
+            "kind": "event_match",
+            "key": "content.body",
+            "pattern": "foobaz",
+        }
+        self._assert_matches(
+            condition,
+            {"body": "aaa FoobaZ zzz"},
+            "patterns should match and be case-insensitive",
+        )
+        self._assert_not_matches(
+            condition,
+            {"body": "aa xFoobaZ yy"},
+            "pattern should only match at word boundaries",
+        )
+        self._assert_not_matches(
+            condition,
+            {"body": "aa foobazx yy"},
+            "pattern should only match at word boundaries",
+        )
+
+        # wildcards should match
+        condition = {
+            "kind": "event_match",
+            "key": "content.body",
+            "pattern": "f?o*baz",
+        }
+
+        self._assert_matches(
+            condition,
+            {"body": "aaa FoobarbaZ zzz"},
+            "* should match string and pattern should be case-insensitive",
+        )
+        self._assert_matches(
+            condition, {"body": "aa foobaz yy"}, "* should match 0 characters"
+        )
+        self._assert_not_matches(
+            condition, {"body": "aa fobbaz yy"}, "? should not match 0 characters"
+        )
+        self._assert_not_matches(
+            condition, {"body": "aa fiiobaz yy"}, "? should not match 2 characters"
+        )
+        self._assert_not_matches(
+            condition,
+            {"body": "aa xfooxbaz yy"},
+            "pattern should only match at word boundaries",
+        )
+        self._assert_not_matches(
+            condition,
+            {"body": "aa fooxbazx yy"},
+            "pattern should only match at word boundaries",
+        )
+
+        # test backslashes
+        condition = {
+            "kind": "event_match",
+            "key": "content.body",
+            "pattern": r"f\oobaz",
+        }
+        self._assert_matches(
+            condition,
+            {"body": r"F\oobaz"},
+            "backslash should match itself",
+        )
+        condition = {
+            "kind": "event_match",
+            "key": "content.body",
+            "pattern": r"f\?obaz",
+        }
+        self._assert_matches(
+            condition,
+            {"body": r"F\oobaz"},
+            r"? after \ should match any character",
+        )
+
+    def test_event_match_non_body(self):
+        """Check that event_match conditions on other keys work as expected"""
+
+        # if the key is anything other than 'content.body', the pattern must match the
+        # whole value.
+
+        # non-wildcards should match
+        condition = {
+            "kind": "event_match",
+            "key": "content.value",
+            "pattern": "foobaz",
+        }
+        self._assert_matches(
+            condition,
+            {"value": "FoobaZ"},
+            "patterns should match and be case-insensitive",
+        )
+        self._assert_not_matches(
+            condition,
+            {"value": "xFoobaZ"},
+            "pattern should only match at the start/end of the value",
+        )
+        self._assert_not_matches(
+            condition,
+            {"value": "FoobaZz"},
+            "pattern should only match at the start/end of the value",
+        )
+
+        # wildcards should match
+        condition = {
+            "kind": "event_match",
+            "key": "content.value",
+            "pattern": "f?o*baz",
+        }
+        self._assert_matches(
+            condition,
+            {"value": "FoobarbaZ"},
+            "* should match string and pattern should be case-insensitive",
+        )
+        self._assert_matches(
+            condition, {"value": "foobaz"}, "* should match 0 characters"
+        )
+        self._assert_not_matches(
+            condition, {"value": "fobbaz"}, "? should not match 0 characters"
+        )
+        self._assert_not_matches(
+            condition, {"value": "fiiobaz"}, "? should not match 2 characters"
+        )
+        self._assert_not_matches(
+            condition,
+            {"value": "xfooxbaz"},
+            "pattern should only match at the start/end of the value",
+        )
+        self._assert_not_matches(
+            condition,
+            {"value": "fooxbazx"},
+            "pattern should only match at the start/end of the value",
+        )
+        self._assert_not_matches(
+            condition,
+            {"value": "x\nfooxbaz"},
+            "pattern should not match after a newline",
+        )
+        self._assert_not_matches(
+            condition,
+            {"value": "fooxbaz\nx"},
+            "pattern should not match before a newline",
+        )
+
     def test_no_body(self):
         """Not having a body shouldn't break the evaluator."""
         evaluator = self._get_evaluator({})
diff --git a/tests/util/test_glob_to_regex.py b/tests/util/test_glob_to_regex.py
new file mode 100644
index 0000000000..220accb92b
--- /dev/null
+++ b/tests/util/test_glob_to_regex.py
@@ -0,0 +1,59 @@
+# Copyright 2021 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.
+from synapse.util import glob_to_regex
+
+from tests.unittest import TestCase
+
+
+class GlobToRegexTestCase(TestCase):
+    def test_literal_match(self):
+        """patterns without wildcards should match"""
+        pat = glob_to_regex("foobaz")
+        self.assertTrue(
+            pat.match("FoobaZ"), "patterns should match and be case-insensitive"
+        )
+        self.assertFalse(
+            pat.match("x foobaz"), "pattern should not match at word boundaries"
+        )
+
+    def test_wildcard_match(self):
+        pat = glob_to_regex("f?o*baz")
+
+        self.assertTrue(
+            pat.match("FoobarbaZ"),
+            "* should match string and pattern should be case-insensitive",
+        )
+        self.assertTrue(pat.match("foobaz"), "* should match 0 characters")
+        self.assertFalse(pat.match("fooxaz"), "the character after * must match")
+        self.assertFalse(pat.match("fobbaz"), "? should not match 0 characters")
+        self.assertFalse(pat.match("fiiobaz"), "? should not match 2 characters")
+
+    def test_multi_wildcard(self):
+        """patterns with multiple wildcards in a row should match"""
+        pat = glob_to_regex("**baz")
+        self.assertTrue(pat.match("agsgsbaz"), "** should match any string")
+        self.assertTrue(pat.match("baz"), "** should match the empty string")
+        self.assertEqual(pat.pattern, r"\A.{0,}baz\Z")
+
+        pat = glob_to_regex("*?baz")
+        self.assertTrue(pat.match("agsgsbaz"), "*? should match any string")
+        self.assertTrue(pat.match("abaz"), "*? should match a single char")
+        self.assertFalse(pat.match("baz"), "*? should not match the empty string")
+        self.assertEqual(pat.pattern, r"\A.{1,}baz\Z")
+
+        pat = glob_to_regex("a?*?*?baz")
+        self.assertTrue(pat.match("a g baz"), "?*?*? should match 3 chars")
+        self.assertFalse(pat.match("a..baz"), "?*?*? should not match 2 chars")
+        self.assertTrue(pat.match("a.gg.baz"), "?*?*? should match 4 chars")
+        self.assertEqual(pat.pattern, r"\Aa.{3,}baz\Z")