diff --git a/src/ContentMessages.tsx b/src/ContentMessages.ts
similarity index 96%
rename from src/ContentMessages.tsx
rename to src/ContentMessages.ts
index 9a2b9ac79c..09b080496d 100644
--- a/src/ContentMessages.tsx
+++ b/src/ContentMessages.ts
@@ -16,7 +16,6 @@ See the License for the specific language governing permissions and
 limitations under the License.
 */
 
-import React from "react";
 import { MatrixClient } from "matrix-js-sdk/src/client";
 import { IUploadOpts } from "matrix-js-sdk/src/@types/requests";
 import { MsgType } from "matrix-js-sdk/src/@types/event";
@@ -24,7 +23,7 @@ import encrypt from "browser-encrypt-attachment";
 import extractPngChunks from "png-chunks-extract";
 import { IAbortablePromise, IImageInfo } from "matrix-js-sdk/src/@types/partials";
 import { logger } from "matrix-js-sdk/src/logger";
-import { IEventRelation, ISendEventResponse } from "matrix-js-sdk/src/matrix";
+import { IEventRelation, ISendEventResponse, MatrixEvent } from "matrix-js-sdk/src/matrix";
 import { THREAD_RELATION_TYPE } from "matrix-js-sdk/src/models/thread";
 
 import { IEncryptedFile, IMediaEventInfo } from "./customisations/models/IMediaEventContent";
@@ -32,7 +31,6 @@ import dis from './dispatcher/dispatcher';
 import * as sdk from './index';
 import { _t } from './languageHandler';
 import Modal from './Modal';
-import RoomViewStore from './stores/RoomViewStore';
 import Spinner from "./components/views/elements/Spinner";
 import { Action } from "./dispatcher/actions";
 import {
@@ -47,6 +45,8 @@ import { BlurhashEncoder } from "./BlurhashEncoder";
 import SettingsStore from "./settings/SettingsStore";
 import { decorateStartSendingTime, sendRoundTripMetric } from "./sendTimePerformanceMetrics";
 import { TimelineRenderingType } from "./contexts/RoomContext";
+import RoomViewStore from "./stores/RoomViewStore";
+import { addReplyToMessageContent } from "./utils/Reply";
 
 const MAX_WIDTH = 800;
 const MAX_HEIGHT = 600;
@@ -457,25 +457,7 @@ export default class ContentMessages {
             return;
         }
 
-        const isQuoting = Boolean(RoomViewStore.getQuotingEvent());
-        if (isQuoting) {
-            // FIXME: Using an import will result in Element crashing
-            const QuestionDialog = sdk.getComponent("dialogs.QuestionDialog");
-            const { finished } = Modal.createTrackedDialog<[boolean]>('Upload Reply Warning', '', QuestionDialog, {
-                title: _t('Replying With Files'),
-                description: (
-                    <div>{ _t(
-                        'At this time it is not possible to reply with a file. ' +
-                        'Would you like to upload this file without replying?',
-                    ) }</div>
-                ),
-                hasCancelButton: true,
-                button: _t("Continue"),
-            });
-            const [shouldUpload] = await finished;
-            if (!shouldUpload) return;
-        }
-
+        const replyToEvent = RoomViewStore.getQuotingEvent();
         if (!this.mediaConfig) { // hot-path optimization to not flash a spinner if we don't need to
             const modal = Modal.createDialog(Spinner, null, 'mx_Dialog_spinner');
             await this.ensureMediaConfigFetched(matrixClient);
@@ -528,7 +510,16 @@ export default class ContentMessages {
                 }
             }
 
-            promBefore = this.sendContentToRoom(file, roomId, relation, matrixClient, promBefore);
+            promBefore = this.sendContentToRoom(file, roomId, relation, matrixClient, replyToEvent, promBefore);
+        }
+
+        if (replyToEvent) {
+            // Clear event being replied to
+            dis.dispatch({
+                action: "reply_to_event",
+                event: null,
+                context,
+            });
         }
 
         // Focus the correct composer
@@ -569,6 +560,7 @@ export default class ContentMessages {
         roomId: string,
         relation: IEventRelation | undefined,
         matrixClient: MatrixClient,
+        replyToEvent: MatrixEvent | undefined,
         promBefore: Promise<any>,
     ) {
         const content: IContent = {
@@ -583,6 +575,12 @@ export default class ContentMessages {
             content["m.relates_to"] = relation;
         }
 
+        if (replyToEvent) {
+            addReplyToMessageContent(content, replyToEvent, {
+                includeLegacyFallback: false,
+            });
+        }
+
         if (SettingsStore.getValue("Performance.addSendMessageTimingMetadata")) {
             decorateStartSendingTime(content);
         }
diff --git a/src/components/views/rooms/SendMessageComposer.tsx b/src/components/views/rooms/SendMessageComposer.tsx
index b6d06f26b1..2bbf8294f7 100644
--- a/src/components/views/rooms/SendMessageComposer.tsx
+++ b/src/components/views/rooms/SendMessageComposer.tsx
@@ -58,35 +58,7 @@ import { ComposerType } from "../../../dispatcher/payloads/ComposerInsertPayload
 import { getSlashCommand, isSlashCommand, runSlashCommand, shouldSendAnyway } from "../../../editor/commands";
 import { KeyBindingAction } from "../../../accessibility/KeyboardShortcuts";
 import { PosthogAnalytics } from "../../../PosthogAnalytics";
-import { getNestedReplyText, makeReplyMixIn } from '../../../utils/Reply';
-
-interface IAddReplyOpts {
-    permalinkCreator?: RoomPermalinkCreator;
-    includeLegacyFallback?: boolean;
-}
-
-function addReplyToMessageContent(
-    content: IContent,
-    replyToEvent: MatrixEvent,
-    opts: IAddReplyOpts = {
-        includeLegacyFallback: true,
-    },
-): void {
-    const replyContent = makeReplyMixIn(replyToEvent);
-    Object.assign(content, replyContent);
-
-    if (opts.includeLegacyFallback) {
-        // Part of Replies fallback support - prepend the text we're sending
-        // with the text we're replying to
-        const nestedReply = getNestedReplyText(replyToEvent, opts.permalinkCreator);
-        if (nestedReply) {
-            if (content.formatted_body) {
-                content.formatted_body = nestedReply.html + content.formatted_body;
-            }
-            content.body = nestedReply.body + content.body;
-        }
-    }
-}
+import { addReplyToMessageContent } from '../../../utils/Reply';
 
 export function attachRelation(
     content: IContent,
diff --git a/src/i18n/strings/en_EN.json b/src/i18n/strings/en_EN.json
index ba3f4ce88d..08332fecda 100644
--- a/src/i18n/strings/en_EN.json
+++ b/src/i18n/strings/en_EN.json
@@ -71,9 +71,6 @@
     "You do not have permission to start a conference call in this room": "You do not have permission to start a conference call in this room",
     "End conference": "End conference",
     "This will end the conference for everyone. Continue?": "This will end the conference for everyone. Continue?",
-    "Replying With Files": "Replying With Files",
-    "At this time it is not possible to reply with a file. Would you like to upload this file without replying?": "At this time it is not possible to reply with a file. Would you like to upload this file without replying?",
-    "Continue": "Continue",
     "The file '%(fileName)s' failed to upload.": "The file '%(fileName)s' failed to upload.",
     "The file '%(fileName)s' exceeds this homeserver's size limit for uploads": "The file '%(fileName)s' exceeds this homeserver's size limit for uploads",
     "Upload Failed": "Upload Failed",
@@ -455,6 +452,7 @@
     "Invites user with given id to current room": "Invites user with given id to current room",
     "Use an identity server": "Use an identity server",
     "Use an identity server to invite by email. Click continue to use the default identity server (%(defaultIdentityServerName)s) or manage in Settings.": "Use an identity server to invite by email. Click continue to use the default identity server (%(defaultIdentityServerName)s) or manage in Settings.",
+    "Continue": "Continue",
     "Use an identity server to invite by email. Manage in Settings.": "Use an identity server to invite by email. Manage in Settings.",
     "Joins room with given address": "Joins room with given address",
     "Leave room": "Leave room",
diff --git a/src/utils/Reply.ts b/src/utils/Reply.ts
index f36a526aa6..7c5d92fc46 100644
--- a/src/utils/Reply.ts
+++ b/src/utils/Reply.ts
@@ -184,3 +184,31 @@ export function shouldDisplayReply(event: MatrixEvent): boolean {
 
     return !!inReplyTo.event_id;
 }
+
+interface IAddReplyOpts {
+    permalinkCreator?: RoomPermalinkCreator;
+    includeLegacyFallback?: boolean;
+}
+
+export function addReplyToMessageContent(
+    content: IContent,
+    replyToEvent: MatrixEvent,
+    opts: IAddReplyOpts = {
+        includeLegacyFallback: true,
+    },
+): void {
+    const replyContent = makeReplyMixIn(replyToEvent);
+    Object.assign(content, replyContent);
+
+    if (opts.includeLegacyFallback) {
+        // Part of Replies fallback support - prepend the text we're sending
+        // with the text we're replying to
+        const nestedReply = getNestedReplyText(replyToEvent, opts.permalinkCreator);
+        if (nestedReply) {
+            if (content.formatted_body) {
+                content.formatted_body = nestedReply.html + content.formatted_body;
+            }
+            content.body = nestedReply.body + content.body;
+        }
+    }
+}