diff --git a/res/css/views/messages/_MessageActionBar.scss b/res/css/views/messages/_MessageActionBar.scss
index 1254b496b5..3ecbef0d1f 100644
--- a/res/css/views/messages/_MessageActionBar.scss
+++ b/res/css/views/messages/_MessageActionBar.scss
@@ -105,3 +105,11 @@ limitations under the License.
 .mx_MessageActionBar_optionsButton::after {
     mask-image: url('$(res)/img/element-icons/context-menu.svg');
 }
+
+.mx_MessageActionBar_resendButton::after {
+    mask-image: url('$(res)/img/element-icons/retry.svg');
+}
+
+.mx_MessageActionBar_cancelButton::after {
+    mask-image: url('$(res)/img/element-icons/trashcan.svg');
+}
diff --git a/res/css/views/rooms/_EventTile.scss b/res/css/views/rooms/_EventTile.scss
index 2b3e179c54..5d1dd04383 100644
--- a/res/css/views/rooms/_EventTile.scss
+++ b/res/css/views/rooms/_EventTile.scss
@@ -214,10 +214,6 @@ $left-gutter: 64px;
     color: $accent-fg-color;
 }
 
-.mx_EventTile_notSent {
-    color: $event-notsent-color;
-}
-
 .mx_EventTile_receiptSent,
 .mx_EventTile_receiptSending {
     // We don't use `position: relative` on the element because then it won't line
diff --git a/src/components/views/context_menus/MessageContextMenu.js b/src/components/views/context_menus/MessageContextMenu.js
index f86cd26f32..142b8c80a8 100644
--- a/src/components/views/context_menus/MessageContextMenu.js
+++ b/src/components/views/context_menus/MessageContextMenu.js
@@ -1,8 +1,6 @@
 /*
-Copyright 2015, 2016 OpenMarket Ltd
-Copyright 2018 New Vector Ltd
 Copyright 2019 Michael Telatynski <7t3chguy@gmail.com>
-Copyright 2019 The Matrix.org Foundation C.I.C.
+Copyright 2015, 2016, 2018, 2019, 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.
@@ -34,7 +32,7 @@ import {MenuItem} from "../../structures/ContextMenu";
 import {EventType} from "matrix-js-sdk/src/@types/event";
 import {replaceableComponent} from "../../../utils/replaceableComponent";
 
-function canCancel(eventStatus) {
+export function canCancel(eventStatus) {
     return eventStatus === EventStatus.QUEUED || eventStatus === EventStatus.NOT_SENT;
 }
 
@@ -98,21 +96,6 @@ export default class MessageContextMenu extends React.Component {
         return content.pinned && Array.isArray(content.pinned) && content.pinned.includes(this.props.mxEvent.getId());
     }
 
-    onResendClick = () => {
-        Resend.resend(this.props.mxEvent);
-        this.closeMenu();
-    };
-
-    onResendEditClick = () => {
-        Resend.resend(this.props.mxEvent.replacingEvent());
-        this.closeMenu();
-    };
-
-    onResendRedactionClick = () => {
-        Resend.resend(this.props.mxEvent.localRedactionEvent());
-        this.closeMenu();
-    };
-
     onResendReactionsClick = () => {
         for (const reaction of this._getUnsentReactions()) {
             Resend.resend(reaction);
@@ -170,29 +153,6 @@ export default class MessageContextMenu extends React.Component {
         this.closeMenu();
     };
 
-    onCancelSendClick = () => {
-        const mxEvent = this.props.mxEvent;
-        const editEvent = mxEvent.replacingEvent();
-        const redactEvent = mxEvent.localRedactionEvent();
-        const pendingReactions = this._getPendingReactions();
-
-        if (editEvent && canCancel(editEvent.status)) {
-            Resend.removeFromQueue(editEvent);
-        }
-        if (redactEvent && canCancel(redactEvent.status)) {
-            Resend.removeFromQueue(redactEvent);
-        }
-        if (pendingReactions.length) {
-            for (const reaction of pendingReactions) {
-                Resend.removeFromQueue(reaction);
-            }
-        }
-        if (canCancel(mxEvent.status)) {
-            Resend.removeFromQueue(this.props.mxEvent);
-        }
-        this.closeMenu();
-    };
-
     onForwardClick = () => {
         if (this.props.onCloseDialog) this.props.onCloseDialog();
         dis.dispatch({
@@ -285,20 +245,9 @@ export default class MessageContextMenu extends React.Component {
         const me = cli.getUserId();
         const mxEvent = this.props.mxEvent;
         const eventStatus = mxEvent.status;
-        const editStatus = mxEvent.replacingEvent() && mxEvent.replacingEvent().status;
-        const redactStatus = mxEvent.localRedactionEvent() && mxEvent.localRedactionEvent().status;
         const unsentReactionsCount = this._getUnsentReactions().length;
-        const pendingReactionsCount = this._getPendingReactions().length;
-        const allowCancel = canCancel(mxEvent.status) ||
-            canCancel(editStatus) ||
-            canCancel(redactStatus) ||
-            pendingReactionsCount !== 0;
-        let resendButton;
-        let resendEditButton;
         let resendReactionsButton;
-        let resendRedactionButton;
         let redactButton;
-        let cancelButton;
         let forwardButton;
         let pinButton;
         let unhidePreviewButton;
@@ -309,22 +258,6 @@ export default class MessageContextMenu extends React.Component {
         // status is SENT before remote-echo, null after
         const isSent = !eventStatus || eventStatus === EventStatus.SENT;
         if (!mxEvent.isRedacted()) {
-            if (eventStatus === EventStatus.NOT_SENT) {
-                resendButton = (
-                    <MenuItem className="mx_MessageContextMenu_field" onClick={this.onResendClick}>
-                        { _t('Resend') }
-                    </MenuItem>
-                );
-            }
-
-            if (editStatus === EventStatus.NOT_SENT) {
-                resendEditButton = (
-                    <MenuItem className="mx_MessageContextMenu_field" onClick={this.onResendEditClick}>
-                        { _t('Resend edit') }
-                    </MenuItem>
-                );
-            }
-
             if (unsentReactionsCount !== 0) {
                 resendReactionsButton = (
                     <MenuItem className="mx_MessageContextMenu_field" onClick={this.onResendReactionsClick}>
@@ -334,14 +267,6 @@ export default class MessageContextMenu extends React.Component {
             }
         }
 
-        if (redactStatus === EventStatus.NOT_SENT) {
-            resendRedactionButton = (
-                <MenuItem className="mx_MessageContextMenu_field" onClick={this.onResendRedactionClick}>
-                    { _t('Resend removal') }
-                </MenuItem>
-            );
-        }
-
         if (isSent && this.state.canRedact) {
             redactButton = (
                 <MenuItem className="mx_MessageContextMenu_field" onClick={this.onRedactClick}>
@@ -350,14 +275,6 @@ export default class MessageContextMenu extends React.Component {
             );
         }
 
-        if (allowCancel) {
-            cancelButton = (
-                <MenuItem className="mx_MessageContextMenu_field" onClick={this.onCancelSendClick}>
-                    { _t('Cancel Sending') }
-                </MenuItem>
-            );
-        }
-
         if (isContentActionable(mxEvent)) {
             forwardButton = (
                 <MenuItem className="mx_MessageContextMenu_field" onClick={this.onForwardClick}>
@@ -455,12 +372,8 @@ export default class MessageContextMenu extends React.Component {
 
         return (
             <div className="mx_MessageContextMenu">
-                { resendButton }
-                { resendEditButton }
                 { resendReactionsButton }
-                { resendRedactionButton }
                 { redactButton }
-                { cancelButton }
                 { forwardButton }
                 { pinButton }
                 { viewSourceButton }
diff --git a/src/components/views/messages/EditHistoryMessage.js b/src/components/views/messages/EditHistoryMessage.js
index e2eda1e12a..dc4e0187d3 100644
--- a/src/components/views/messages/EditHistoryMessage.js
+++ b/src/components/views/messages/EditHistoryMessage.js
@@ -160,7 +160,6 @@ export default class EditHistoryMessage extends React.PureComponent {
             "mx_EventTile": true,
             // Note: we keep the `sending` state class for tests, not for our styles
             "mx_EventTile_sending": isSending,
-            "mx_EventTile_notSent": this.state.sendStatus === 'not_sent',
         });
         return (
             <li>
diff --git a/src/components/views/messages/MessageActionBar.js b/src/components/views/messages/MessageActionBar.js
index 5a6e7d87b7..b2f7f8a692 100644
--- a/src/components/views/messages/MessageActionBar.js
+++ b/src/components/views/messages/MessageActionBar.js
@@ -29,6 +29,8 @@ import RoomContext from "../../../contexts/RoomContext";
 import Toolbar from "../../../accessibility/Toolbar";
 import {RovingAccessibleTooltipButton, useRovingTabIndex} from "../../../accessibility/RovingTabIndex";
 import {replaceableComponent} from "../../../utils/replaceableComponent";
+import {canCancel} from "../context_menus/MessageContextMenu";
+import Resend from "../../../Resend";
 
 const OptionsButton = ({mxEvent, getTile, getReplyThread, permalinkCreator, onFocusChange}) => {
     const [menuDisplayed, button, openMenu, closeMenu] = useContextMenu();
@@ -169,45 +171,118 @@ export default class MessageActionBar extends React.PureComponent {
         });
     };
 
-    render() {
-        let reactButton;
-        let replyButton;
-        let editButton;
+    /**
+     * Runs a given fn on the set of possible events to test. The first event
+     * that passes the checkFn will have fn executed on it. Both functions take
+     * a MatrixEvent object. If no particular conditions are needed, checkFn can
+     * be null/undefined. If no functions pass the checkFn, no action will be
+     * taken.
+     * @param {Function} fn The execution function.
+     * @param {Function} checkFn The test function.
+     */
+    runActionOnFailedEv(fn, checkFn) {
+        if (!checkFn) checkFn = () => true;
 
-        if (isContentActionable(this.props.mxEvent)) {
-            if (this.context.canReact) {
-                reactButton = (
-                    <ReactButton mxEvent={this.props.mxEvent} reactions={this.props.reactions} onFocusChange={this.onFocusChange} />
-                );
-            }
-            if (this.context.canReply) {
-                replyButton = <RovingAccessibleTooltipButton
-                    className="mx_MessageActionBar_maskButton mx_MessageActionBar_replyButton"
-                    title={_t("Reply")}
-                    onClick={this.onReplyClick}
-                />;
+        const mxEvent = this.props.mxEvent;
+        const editEvent = mxEvent.replacingEvent();
+        const redactEvent = mxEvent.localRedactionEvent();
+        const tryOrder = [redactEvent, editEvent, mxEvent];
+        for (const ev of tryOrder) {
+            if (ev && checkFn(ev)) {
+                fn(ev);
+                break;
             }
         }
+    }
+
+    onResendClick = (ev) => {
+        this.runActionOnFailedEv((tarEv) => Resend.resend(tarEv));
+    };
+
+    onCancelClick = (ev) => {
+        this.runActionOnFailedEv(
+            (tarEv) => Resend.removeFromQueue(tarEv),
+            (testEv) => canCancel(testEv.status),
+        );
+    };
+
+    render() {
+        const toolbarOpts = [];
         if (canEditContent(this.props.mxEvent)) {
-            editButton = <RovingAccessibleTooltipButton
+            toolbarOpts.push(<RovingAccessibleTooltipButton
                 className="mx_MessageActionBar_maskButton mx_MessageActionBar_editButton"
                 title={_t("Edit")}
                 onClick={this.onEditClick}
-            />;
+                key="edit"
+            />);
         }
 
-        // aria-live=off to not have this read out automatically as navigating around timeline, gets repetitive.
-        return <Toolbar className="mx_MessageActionBar" aria-label={_t("Message Actions")} aria-live="off">
-            {reactButton}
-            {replyButton}
-            {editButton}
-            <OptionsButton
+        const cancelSendingButton = <RovingAccessibleTooltipButton
+            className="mx_MessageActionBar_maskButton mx_MessageActionBar_cancelButton"
+            title={_t("Delete")}
+            onClick={this.onCancelClick}
+            key="cancel"
+        />;
+
+        // We show a different toolbar for failed events, so detect that first.
+        const mxEvent = this.props.mxEvent;
+        const editStatus = mxEvent.replacingEvent() && mxEvent.replacingEvent().status;
+        const redactStatus = mxEvent.localRedactionEvent() && mxEvent.localRedactionEvent().status;
+        const allowCancel = canCancel(mxEvent.status) || canCancel(editStatus) || canCancel(redactStatus);
+        const isFailed = [mxEvent.status, editStatus, redactStatus].includes("not_sent");
+        if (allowCancel && isFailed) {
+            // The resend button needs to appear ahead of the edit button, so insert to the
+            // start of the opts
+            toolbarOpts.splice(0, 0, <RovingAccessibleTooltipButton
+                className="mx_MessageActionBar_maskButton mx_MessageActionBar_resendButton"
+                title={_t("Retry")}
+                onClick={this.onResendClick}
+                key="resend"
+            />);
+
+            // The delete button should appear last, so we can just drop it at the end
+            toolbarOpts.push(cancelSendingButton);
+        } else {
+            if (isContentActionable(this.props.mxEvent)) {
+                // Like the resend button, the react and reply buttons need to appear before the edit.
+                // The only catch is we do the reply button first so that we can make sure the react
+                // button is the very first button without having to do length checks for `splice()`.
+                if (this.context.canReply) {
+                    toolbarOpts.splice(0, 0, <RovingAccessibleTooltipButton
+                        className="mx_MessageActionBar_maskButton mx_MessageActionBar_replyButton"
+                        title={_t("Reply")}
+                        onClick={this.onReplyClick}
+                        key="reply"
+                    />);
+                }
+                if (this.context.canReact) {
+                    toolbarOpts.splice(0, 0, <ReactButton
+                        mxEvent={this.props.mxEvent}
+                        reactions={this.props.reactions}
+                        onFocusChange={this.onFocusChange}
+                        key="react"
+                    />);
+                }
+            }
+
+            if (allowCancel) {
+                toolbarOpts.push(cancelSendingButton);
+            }
+
+            // The menu button should be last, so dump it there.
+            toolbarOpts.push(<OptionsButton
                 mxEvent={this.props.mxEvent}
                 getReplyThread={this.props.getReplyThread}
                 getTile={this.props.getTile}
                 permalinkCreator={this.props.permalinkCreator}
                 onFocusChange={this.onFocusChange}
-            />
+                key="menu"
+            />);
+        }
+
+        // aria-live=off to not have this read out automatically as navigating around timeline, gets repetitive.
+        return <Toolbar className="mx_MessageActionBar" aria-label={_t("Message Actions")} aria-live="off">
+            {toolbarOpts}
         </Toolbar>;
     }
 }
diff --git a/src/components/views/rooms/EventTile.js b/src/components/views/rooms/EventTile.js
index f6fb83c064..05afb742a4 100644
--- a/src/components/views/rooms/EventTile.js
+++ b/src/components/views/rooms/EventTile.js
@@ -40,6 +40,9 @@ import {WIDGET_LAYOUT_EVENT_TYPE} from "../../../stores/widgets/WidgetLayoutStor
 import {objectHasDiff} from "../../../utils/objects";
 import {replaceableComponent} from "../../../utils/replaceableComponent";
 import Tooltip from "../elements/Tooltip";
+import {StaticNotificationState} from "../../../stores/notifications/StaticNotificationState";
+import {NotificationColor} from "../../../stores/notifications/NotificationColor";
+import NotificationBadge from "./NotificationBadge";
 
 const eventTileTypes = {
     [EventType.RoomMessage]: 'messages.MessageEvent',
@@ -838,7 +841,6 @@ export default class EventTile extends React.Component {
             mx_EventTile_12hr: this.props.isTwelveHour,
             // Note: we keep the `sending` state class for tests, not for our styles
             mx_EventTile_sending: !isEditing && isSending,
-            mx_EventTile_notSent: this.props.eventSendStatus === 'not_sent',
             mx_EventTile_highlight: this.props.tileShape === 'notif' ? false : this.shouldHighlight(),
             mx_EventTile_selected: this.props.isSelectedEvent,
             mx_EventTile_continuation: this.props.tileShape ? '' : this.props.continuation,
@@ -1253,11 +1255,19 @@ class SentReceipt extends React.PureComponent<ISentReceiptProps, ISentReceiptSta
 
     render() {
         const isSent = !this.props.messageState || this.props.messageState === 'sent';
+        const isFailed = this.props.messageState === 'not_sent';
         const receiptClasses = classNames({
             'mx_EventTile_receiptSent': isSent,
-            'mx_EventTile_receiptSending': !isSent,
+            'mx_EventTile_receiptSending': !isSent && !isFailed,
         });
 
+        let nonCssBadge = null;
+        if (isFailed) {
+            nonCssBadge = <NotificationBadge
+                notification={StaticNotificationState.forSymbol("!", NotificationColor.Red)}
+            />;
+        }
+
         let tooltip = null;
         if (this.state.hover) {
             let label = _t("Sending your message...");
@@ -1265,6 +1275,8 @@ class SentReceipt extends React.PureComponent<ISentReceiptProps, ISentReceiptSta
                 label = _t("Encrypting your message...");
             } else if (isSent) {
                 label = _t("Your message was sent");
+            } else if (isFailed) {
+                label = _t("Failed to send");
             }
             // The yOffset is somewhat arbitrary - it just brings the tooltip down to be more associated
             // with the read receipt.
@@ -1273,6 +1285,7 @@ class SentReceipt extends React.PureComponent<ISentReceiptProps, ISentReceiptSta
 
         return <span className="mx_EventTile_readAvatars">
             <span className={receiptClasses} onMouseEnter={this.onHoverStart} onMouseLeave={this.onHoverEnd}>
+                {nonCssBadge}
                 {tooltip}
             </span>
         </span>;
diff --git a/src/i18n/strings/en_EN.json b/src/i18n/strings/en_EN.json
index 0b525670a8..7af06aa5b1 100644
--- a/src/i18n/strings/en_EN.json
+++ b/src/i18n/strings/en_EN.json
@@ -1452,6 +1452,7 @@
     "Sending your message...": "Sending your message...",
     "Encrypting your message...": "Encrypting your message...",
     "Your message was sent": "Your message was sent",
+    "Failed to send": "Failed to send",
     "Please select the destination room for this message": "Please select the destination room for this message",
     "Scroll to most recent messages": "Scroll to most recent messages",
     "Close preview": "Close preview",
@@ -1810,8 +1811,9 @@
     "The encryption used by this room isn't supported.": "The encryption used by this room isn't supported.",
     "Error decrypting audio": "Error decrypting audio",
     "React": "React",
-    "Reply": "Reply",
     "Edit": "Edit",
+    "Retry": "Retry",
+    "Reply": "Reply",
     "Message Actions": "Message Actions",
     "Attachment": "Attachment",
     "Error decrypting attachment": "Error decrypting attachment",
@@ -2390,7 +2392,6 @@
     "Confirm encryption setup": "Confirm encryption setup",
     "Click the button below to confirm setting up encryption.": "Click the button below to confirm setting up encryption.",
     "Unable to set up keys": "Unable to set up keys",
-    "Retry": "Retry",
     "Restoring keys from backup": "Restoring keys from backup",
     "Fetching keys from server...": "Fetching keys from server...",
     "%(completed)s of %(total)s keys restored": "%(completed)s of %(total)s keys restored",
@@ -2419,10 +2420,7 @@
     "Reject invitation": "Reject invitation",
     "Are you sure you want to reject the invitation?": "Are you sure you want to reject the invitation?",
     "Unable to reject invite": "Unable to reject invite",
-    "Resend edit": "Resend edit",
     "Resend %(unsentCount)s reaction(s)": "Resend %(unsentCount)s reaction(s)",
-    "Resend removal": "Resend removal",
-    "Cancel Sending": "Cancel Sending",
     "Forward Message": "Forward Message",
     "Pin Message": "Pin Message",
     "Unhide Preview": "Unhide Preview",