diff --git a/res/css/views/context_menus/_MessageContextMenu.pcss b/res/css/views/context_menus/_MessageContextMenu.pcss
index be113c770f6c..28529eabf983 100644
--- a/res/css/views/context_menus/_MessageContextMenu.pcss
+++ b/res/css/views/context_menus/_MessageContextMenu.pcss
@@ -81,11 +81,11 @@ limitations under the License.
     }
 
     .mx_MessageContextMenu_iconPin::before {
-        mask-image: url("$(res)/img/element-icons/room/pin-upright.svg");
+        mask-image: url("@vector-im/compound-design-tokens/icons/pin.svg");
     }
 
     .mx_MessageContextMenu_iconUnpin::before {
-        mask-image: url("$(res)/img/element-icons/room/pin.svg");
+        mask-image: url("@vector-im/compound-design-tokens/icons/unpin.svg");
     }
 
     .mx_MessageContextMenu_iconCopy::before {
diff --git a/src/components/views/context_menus/MessageContextMenu.tsx b/src/components/views/context_menus/MessageContextMenu.tsx
index 801ab0b023e7..2d5a81a89b62 100644
--- a/src/components/views/context_menus/MessageContextMenu.tsx
+++ b/src/components/views/context_menus/MessageContextMenu.tsx
@@ -36,9 +36,8 @@ import Modal from "../../../Modal";
 import Resend from "../../../Resend";
 import SettingsStore from "../../../settings/SettingsStore";
 import { isUrlPermitted } from "../../../HtmlUtils";
-import { canEditContent, canPinEvent, editEvent, isContentActionable } from "../../../utils/EventUtils";
+import { canEditContent, editEvent, isContentActionable } from "../../../utils/EventUtils";
 import IconizedContextMenu, { IconizedContextMenuOption, IconizedContextMenuOptionList } from "./IconizedContextMenu";
-import { ReadPinsEventId } from "../right_panel/types";
 import { Action } from "../../../dispatcher/actions";
 import { RoomPermalinkCreator } from "../../../utils/permalinks/Permalinks";
 import { ButtonEvent } from "../elements/AccessibleButton";
@@ -60,6 +59,7 @@ import { getForwardableEvent } from "../../../events/forward/getForwardableEvent
 import { getShareableLocationEvent } from "../../../events/location/getShareableLocationEvent";
 import { ShowThreadPayload } from "../../../dispatcher/payloads/ShowThreadPayload";
 import { CardContext } from "../right_panel/context";
+import PinningUtils from "../../../utils/PinningUtils";
 
 interface IReplyInThreadButton {
     mxEvent: MatrixEvent;
@@ -177,24 +177,11 @@ export default class MessageContextMenu extends React.Component<IProps, IState>
             this.props.mxEvent.getType() !== EventType.RoomServerAcl &&
             this.props.mxEvent.getType() !== EventType.RoomEncryption;
 
-        let canPin =
-            !!room?.currentState.mayClientSendStateEvent(EventType.RoomPinnedEvents, cli) &&
-            canPinEvent(this.props.mxEvent);
-
-        // HACK: Intentionally say we can't pin if the user doesn't want to use the functionality
-        if (!SettingsStore.getValue("feature_pinning")) canPin = false;
+        const canPin = PinningUtils.canPinOrUnpin(cli, this.props.mxEvent);
 
         this.setState({ canRedact, canPin });
     };
 
-    private isPinned(): boolean {
-        const room = MatrixClientPeg.safeGet().getRoom(this.props.mxEvent.getRoomId());
-        const pinnedEvent = room?.currentState.getStateEvents(EventType.RoomPinnedEvents, "");
-        if (!pinnedEvent) return false;
-        const content = pinnedEvent.getContent();
-        return content.pinned && Array.isArray(content.pinned) && content.pinned.includes(this.props.mxEvent.getId());
-    }
-
     private canEndPoll(mxEvent: MatrixEvent): boolean {
         return (
             M_POLL_START.matches(mxEvent.getType()) &&
@@ -257,22 +244,8 @@ export default class MessageContextMenu extends React.Component<IProps, IState>
     };
 
     private onPinClick = (): void => {
-        const cli = MatrixClientPeg.safeGet();
-        const room = cli.getRoom(this.props.mxEvent.getRoomId());
-        if (!room) return;
-        const eventId = this.props.mxEvent.getId();
-
-        const pinnedIds = room.currentState?.getStateEvents(EventType.RoomPinnedEvents, "")?.getContent().pinned || [];
-
-        if (pinnedIds.includes(eventId)) {
-            pinnedIds.splice(pinnedIds.indexOf(eventId), 1);
-        } else {
-            pinnedIds.push(eventId);
-            cli.setRoomAccountData(room.roomId, ReadPinsEventId, {
-                event_ids: [...(room.getAccountData(ReadPinsEventId)?.getContent()?.event_ids || []), eventId],
-            });
-        }
-        cli.sendStateEvent(room.roomId, EventType.RoomPinnedEvents, { pinned: pinnedIds }, "");
+        // Pin or unpin in background
+        PinningUtils.pinOrUnpinEvent(MatrixClientPeg.safeGet(), this.props.mxEvent);
         this.closeMenu();
     };
 
@@ -452,17 +425,6 @@ export default class MessageContextMenu extends React.Component<IProps, IState>
             );
         }
 
-        let pinButton: JSX.Element | undefined;
-        if (contentActionable && this.state.canPin) {
-            pinButton = (
-                <IconizedContextMenuOption
-                    iconClassName="mx_MessageContextMenu_iconPin"
-                    label={this.isPinned() ? _t("action|unpin") : _t("action|pin")}
-                    onClick={this.onPinClick}
-                />
-            );
-        }
-
         // This is specifically not behind the developerMode flag to give people insight into the Matrix
         const viewSourceButton = (
             <IconizedContextMenuOption
@@ -649,6 +611,18 @@ export default class MessageContextMenu extends React.Component<IProps, IState>
             );
         }
 
+        let pinButton: JSX.Element | undefined;
+        if (rightClick && this.state.canPin) {
+            const isPinned = PinningUtils.isPinned(MatrixClientPeg.safeGet(), this.props.mxEvent);
+            pinButton = (
+                <IconizedContextMenuOption
+                    iconClassName={isPinned ? "mx_MessageContextMenu_iconUnpin" : "mx_MessageContextMenu_iconPin"}
+                    label={isPinned ? _t("action|unpin") : _t("action|pin")}
+                    onClick={this.onPinClick}
+                />
+            );
+        }
+
         let viewInRoomButton: JSX.Element | undefined;
         if (isThreadRootEvent) {
             viewInRoomButton = (
@@ -671,13 +645,14 @@ export default class MessageContextMenu extends React.Component<IProps, IState>
         }
 
         let quickItemsList: JSX.Element | undefined;
-        if (editButton || replyButton || reactButton) {
+        if (editButton || replyButton || reactButton || pinButton) {
             quickItemsList = (
                 <IconizedContextMenuOptionList>
                     {reactButton}
                     {replyButton}
                     {replyInThreadButton}
                     {editButton}
+                    {pinButton}
                 </IconizedContextMenuOptionList>
             );
         }
@@ -688,7 +663,6 @@ export default class MessageContextMenu extends React.Component<IProps, IState>
                 {openInMapSiteButton}
                 {endPollButton}
                 {forwardButton}
-                {pinButton}
                 {permalinkButton}
                 {reportEventButton}
                 {externalURLButton}
diff --git a/src/components/views/messages/MessageActionBar.tsx b/src/components/views/messages/MessageActionBar.tsx
index 25547c78363d..20a87abc9d0c 100644
--- a/src/components/views/messages/MessageActionBar.tsx
+++ b/src/components/views/messages/MessageActionBar.tsx
@@ -26,6 +26,8 @@ import {
     M_BEACON_INFO,
 } from "matrix-js-sdk/src/matrix";
 import classNames from "classnames";
+import { Icon as PinIcon } from "@vector-im/compound-design-tokens/icons/pin.svg";
+import { Icon as UnpinIcon } from "@vector-im/compound-design-tokens/icons/unpin.svg";
 
 import { Icon as ContextMenuIcon } from "../../../../res/img/element-icons/context-menu.svg";
 import { Icon as EditIcon } from "../../../../res/img/element-icons/room/message-bar/edit.svg";
@@ -61,6 +63,7 @@ import { ShowThreadPayload } from "../../../dispatcher/payloads/ShowThreadPayloa
 import { GetRelationsForEvent, IEventTileType } from "../rooms/EventTile";
 import { VoiceBroadcastInfoEventType } from "../../../voice-broadcast/types";
 import { ButtonEvent } from "../elements/AccessibleButton";
+import PinningUtils from "../../../utils/PinningUtils";
 
 interface IOptionsButtonProps {
     mxEvent: MatrixEvent;
@@ -384,6 +387,13 @@ export default class MessageActionBar extends React.PureComponent<IMessageAction
         );
     };
 
+    /**
+     * Pin or unpin the event.
+     */
+    private onPinClick = async (): Promise<void> => {
+        await PinningUtils.pinOrUnpinEvent(MatrixClientPeg.safeGet(), this.props.mxEvent);
+    };
+
     public render(): React.ReactNode {
         const toolbarOpts: JSX.Element[] = [];
         if (canEditContent(MatrixClientPeg.safeGet(), this.props.mxEvent)) {
@@ -401,6 +411,22 @@ export default class MessageActionBar extends React.PureComponent<IMessageAction
             );
         }
 
+        if (PinningUtils.canPinOrUnpin(MatrixClientPeg.safeGet(), this.props.mxEvent)) {
+            const isPinned = PinningUtils.isPinned(MatrixClientPeg.safeGet(), this.props.mxEvent);
+            toolbarOpts.push(
+                <RovingAccessibleButton
+                    className="mx_MessageActionBar_iconButton"
+                    title={isPinned ? _t("action|unpin") : _t("action|pin")}
+                    onClick={this.onPinClick}
+                    onContextMenu={this.onPinClick}
+                    key="pin"
+                    placement="left"
+                >
+                    {isPinned ? <UnpinIcon /> : <PinIcon />}
+                </RovingAccessibleButton>,
+            );
+        }
+
         const cancelSendingButton = (
             <RovingAccessibleButton
                 className="mx_MessageActionBar_iconButton"
diff --git a/src/utils/PinningUtils.ts b/src/utils/PinningUtils.ts
index f9750a3ed228..eb962397e6cf 100644
--- a/src/utils/PinningUtils.ts
+++ b/src/utils/PinningUtils.ts
@@ -14,7 +14,11 @@ See the License for the specific language governing permissions and
 limitations under the License.
 */
 
-import { MatrixEvent, EventType, M_POLL_START } from "matrix-js-sdk/src/matrix";
+import { MatrixEvent, EventType, M_POLL_START, MatrixClient, EventTimeline } from "matrix-js-sdk/src/matrix";
+
+import { canPinEvent, isContentActionable } from "./EventUtils";
+import SettingsStore from "../settings/SettingsStore";
+import { ReadPinsEventId } from "../components/views/right_panel/types";
 
 export default class PinningUtils {
     /**
@@ -38,4 +42,75 @@ export default class PinningUtils {
 
         return true;
     }
+
+    /**
+     * Determines if the given event is pinned.
+     * @param matrixClient
+     * @param mxEvent
+     */
+    public static isPinned(matrixClient: MatrixClient, mxEvent: MatrixEvent): boolean {
+        const room = matrixClient.getRoom(mxEvent.getRoomId());
+        if (!room) return false;
+
+        const pinnedEvent = room
+            .getLiveTimeline()
+            .getState(EventTimeline.FORWARDS)
+            ?.getStateEvents(EventType.RoomPinnedEvents, "");
+        if (!pinnedEvent) return false;
+        const content = pinnedEvent.getContent();
+        return content.pinned && Array.isArray(content.pinned) && content.pinned.includes(mxEvent.getId());
+    }
+
+    /**
+     * Determines if the given event may be pinned or unpinned.
+     * @param matrixClient
+     * @param mxEvent
+     */
+    public static canPinOrUnpin(matrixClient: MatrixClient, mxEvent: MatrixEvent): boolean {
+        if (!SettingsStore.getValue("feature_pinning")) return false;
+        if (!isContentActionable(mxEvent)) return false;
+
+        const room = matrixClient.getRoom(mxEvent.getRoomId());
+        if (!room) return false;
+
+        return Boolean(
+            room
+                .getLiveTimeline()
+                .getState(EventTimeline.FORWARDS)
+                ?.mayClientSendStateEvent(EventType.RoomPinnedEvents, matrixClient) && canPinEvent(mxEvent),
+        );
+    }
+
+    /**
+     * Pin or unpin the given event.
+     * @param matrixClient
+     * @param mxEvent
+     */
+    public static async pinOrUnpinEvent(matrixClient: MatrixClient, mxEvent: MatrixEvent): Promise<void> {
+        const room = matrixClient.getRoom(mxEvent.getRoomId());
+        if (!room) return;
+
+        const eventId = mxEvent.getId();
+        if (!eventId) return;
+
+        // Get the current pinned events of the room
+        const pinnedIds: Array<string> =
+            room
+                .getLiveTimeline()
+                .getState(EventTimeline.FORWARDS)
+                ?.getStateEvents(EventType.RoomPinnedEvents, "")
+                ?.getContent().pinned || [];
+
+        // If the event is already pinned, unpin it
+        if (pinnedIds.includes(eventId)) {
+            pinnedIds.splice(pinnedIds.indexOf(eventId), 1);
+        } else {
+            // Otherwise, pin it
+            pinnedIds.push(eventId);
+            await matrixClient.setRoomAccountData(room.roomId, ReadPinsEventId, {
+                event_ids: [...(room.getAccountData(ReadPinsEventId)?.getContent()?.event_ids || []), eventId],
+            });
+        }
+        await matrixClient.sendStateEvent(room.roomId, EventType.RoomPinnedEvents, { pinned: pinnedIds }, "");
+    }
 }