diff --git a/src/ContentMessages.tsx b/src/ContentMessages.tsx
index 99be5174f6d..3d9b29ac154 100644
--- a/src/ContentMessages.tsx
+++ b/src/ContentMessages.tsx
@@ -39,6 +39,7 @@ import {
 import { IUpload } from "./models/IUpload";
 import { IAbortablePromise, IImageInfo } from "matrix-js-sdk/src/@types/partials";
 import { BlurhashEncoder } from "./BlurhashEncoder";
+import SettingsStore from "./settings/SettingsStore";
 
 const MAX_WIDTH = 800;
 const MAX_HEIGHT = 600;
@@ -442,7 +443,7 @@ export default class ContentMessages {
         }
 
         const isQuoting = Boolean(RoomViewStore.getQuotingEvent());
-        if (isQuoting) {
+        if (isQuoting && !SettingsStore.getValue("feature_message_attachments")) {
             // FIXME: Using an import will result in Element crashing
             const QuestionDialog = sdk.getComponent("dialogs.QuestionDialog");
             const { finished } = Modal.createTrackedDialog<[boolean]>('Upload Reply Warning', '', QuestionDialog, {
diff --git a/src/components/structures/RoomView.tsx b/src/components/structures/RoomView.tsx
index 03170584864..7ca9f8c09d3 100644
--- a/src/components/structures/RoomView.tsx
+++ b/src/components/structures/RoomView.tsx
@@ -754,7 +754,7 @@ export default class RoomView extends React.Component<IProps, IState> {
                 break;
             case 'picture_snapshot': {
                 const promAfter = (SettingsStore.getValue("feature_message_attachments") && this.messageComposer
-                    && !this.messageComposer.state.isComposerEmpty) ?
+                    && (!this.messageComposer.state.isComposerEmpty || this.messageComposer.props.replyToEvent)) ?
                     (event: ISendEventResponse) => {
                         return this.messageComposer.sendMessage(event.event_id);
                     } : null;
@@ -1255,7 +1255,8 @@ export default class RoomView extends React.Component<IProps, IState> {
         ev.stopPropagation();
         ev.preventDefault();
         const promAfter = (SettingsStore.getValue("feature_message_attachments") && this.messageComposer
-            && ev.dataTransfer.files.length === 1 && !this.messageComposer.state.isComposerEmpty) ?
+            && ev.dataTransfer.files.length === 1
+            && (!this.messageComposer.state.isComposerEmpty || this.messageComposer.props.replyToEvent)) ?
             (event: ISendEventResponse) => {
                 return this.messageComposer.sendMessage(event.event_id);
             } : null;
diff --git a/src/components/views/rooms/MessageComposer.tsx b/src/components/views/rooms/MessageComposer.tsx
index 07cc465f8f9..b57afc5c434 100644
--- a/src/components/views/rooms/MessageComposer.tsx
+++ b/src/components/views/rooms/MessageComposer.tsx
@@ -150,7 +150,8 @@ class UploadButton extends React.Component<IUploadButtonProps> {
         }
 
         const promAfter = (SettingsStore.getValue("feature_message_attachments") && this.props.composer
-            && ev.target.files.length === 1 && !this.props.composer.state.isComposerEmpty) ?
+            && ev.target.files.length === 1
+            && (!this.props.composer.state.isComposerEmpty || this.props.composer.props.replyToEvent)) ?
             (event: ISendEventResponse) => {
                 return this.props.composer.sendMessage(event.event_id);
             } : null;
diff --git a/src/components/views/rooms/SendMessageComposer.tsx b/src/components/views/rooms/SendMessageComposer.tsx
index 7519729e53a..90830fba913 100644
--- a/src/components/views/rooms/SendMessageComposer.tsx
+++ b/src/components/views/rooms/SendMessageComposer.tsx
@@ -55,6 +55,7 @@ import ErrorDialog from "../dialogs/ErrorDialog";
 import QuestionDialog from "../dialogs/QuestionDialog";
 import { ActionPayload } from "../../../dispatcher/payloads";
 import { ISendEventResponse } from 'matrix-js-sdk/src/@types/requests';
+import DocumentOffset from '../../../editor/offset';
 
 function addReplyToMessageContent(
     content: IContent,
@@ -110,15 +111,18 @@ export function createMessageContent(
         body: body,
     };
     const formattedBody = htmlSerializeIfNeeded(model, { forceHTML: !!replyToEvent });
-    if (formattedBody) {
+    if (formattedBody || replyToEvent) {
         content.format = "org.matrix.custom.html";
-        content.formatted_body = formattedBody;
+        content.formatted_body = formattedBody || body;
     }
 
     if (replyToEvent) {
         addReplyToMessageContent(content, replyToEvent, permalinkCreator);
     }
 
+    // TODO: Currently, an attachment will override a reply.
+    // This allows replying with images, but removes the reply relation from the message.
+    // When/if we get the ability to add multiple relations, this will be fixed.
     if (attachEventId) {
         addAttachmentToMessageContent(content, attachEventId);
     }
@@ -363,7 +367,12 @@ export default class SendMessageComposer extends React.Component<IProps> {
 
     public async sendMessage(attachmentEventId?: string): Promise<void> {
         if (this.model.isEmpty) {
-            return;
+            if (!attachmentEventId) {
+                return;
+            }
+            // If replying with just an attachment, add empty text to model so it has at least one part.
+            // Otherwise, various functions expecting at least one part will fail.
+            this.model.update(" ", "insertText", new DocumentOffset(1, true));
         }
 
         const replyToEvent = this.props.replyToEvent;
@@ -543,8 +552,8 @@ export default class SendMessageComposer extends React.Component<IProps> {
         // We check text/rtf instead of text/plain as when copy+pasting a file from Finder or Gnome Image Viewer
         // it puts the filename in as text/plain which we want to ignore.
         if (clipboardData.files.length && !clipboardData.types.includes("text/rtf")) {
-            const promAfter = (SettingsStore.getValue("feature_message_attachents")
-                && clipboardData.files.length === 1 && !this.model.isEmpty) ?
+            const promAfter = (SettingsStore.getValue("feature_message_attachments")
+                && clipboardData.files.length === 1 && (!this.model.isEmpty || this.props.replyToEvent)) ?
                 (event: ISendEventResponse) => {
                     return this.sendMessage(event.event_id);
                 } : null;