diff --git a/app/soapbox/features/chats/components/chat-composer.tsx b/app/soapbox/features/chats/components/chat-composer.tsx
index 0db5ed158..58e93b395 100644
--- a/app/soapbox/features/chats/components/chat-composer.tsx
+++ b/app/soapbox/features/chats/components/chat-composer.tsx
@@ -10,7 +10,6 @@ import { useAppDispatch, useAppSelector } from 'soapbox/hooks';
 const messages = defineMessages({
   placeholder: { id: 'chat.input.placeholder', defaultMessage: 'Type a message' },
   send: { id: 'chat.actions.send', defaultMessage: 'Send' },
-  failedToSend: { id: 'chat.failed_to_send', defaultMessage: 'Message failed to send.' },
   retry: { id: 'chat.retry', defaultMessage: 'Retry?' },
   blocked: { id: 'chat_message_list.blocked', defaultMessage: 'You blocked this user' },
   unblock: { id: 'chat_composer.unblock', defaultMessage: 'Unblock' },
@@ -20,9 +19,9 @@ const messages = defineMessages({
 });
 
 interface IChatComposer extends Pick<React.TextareaHTMLAttributes<HTMLTextAreaElement>, 'onKeyDown' | 'onChange' | 'disabled'> {
-  value: string,
-  onSubmit: () => void,
-  hasErrorSubmittingMessage?: boolean,
+  value: string
+  onSubmit: () => void
+  errorMessage: string | undefined
 }
 
 /** Textarea input for chats. */
@@ -31,7 +30,7 @@ const ChatComposer = React.forwardRef<HTMLTextAreaElement | null, IChatComposer>
   onChange,
   value,
   onSubmit,
-  hasErrorSubmittingMessage = false,
+  errorMessage = false,
   disabled = false,
 }, ref) => {
   const dispatch = useAppDispatch();
@@ -102,10 +101,10 @@ const ChatComposer = React.forwardRef<HTMLTextAreaElement | null, IChatComposer>
       </HStack>
 
       <HStack alignItems='center' className='h-5' space={1}>
-        {hasErrorSubmittingMessage && (
+        {errorMessage && (
           <>
             <Text theme='danger' size='xs'>
-              {intl.formatMessage(messages.failedToSend)}
+              {errorMessage}
             </Text>
 
             <button onClick={onSubmit} className='flex hover:underline'>
diff --git a/app/soapbox/features/chats/components/chat.tsx b/app/soapbox/features/chats/components/chat.tsx
index d99447671..ab0b81abf 100644
--- a/app/soapbox/features/chats/components/chat.tsx
+++ b/app/soapbox/features/chats/components/chat.tsx
@@ -1,5 +1,7 @@
+import { AxiosError } from 'axios';
 import classNames from 'clsx';
 import React, { MutableRefObject, useEffect, useState } from 'react';
+import { defineMessages, useIntl } from 'react-intl';
 
 import { Stack } from 'soapbox/components/ui';
 // import UploadProgress from 'soapbox/components/upload-progress';
@@ -12,17 +14,39 @@ import ChatMessageList from './chat-message-list';
 
 // const fileKeyGen = (): number => Math.floor((Math.random() * 0x10000));
 
+const messages = defineMessages({
+  failedToSend: { id: 'chat.failed_to_send', defaultMessage: 'Message failed to send.' },
+});
+
 interface ChatInterface {
   chat: IChat,
   inputRef?: MutableRefObject<HTMLTextAreaElement | null>,
   className?: string,
 }
 
+/**
+ * Clears the value of the input while dispatching the `onChange` function
+ * which allows the <Textarea> to resize itself (this is important)
+ * because we autoGrow the element as the user inputs text that spans
+ * beyond one line
+ */
+const clearNativeInputValue = (element: HTMLTextAreaElement) => {
+  const nativeInputValueSetter = Object.getOwnPropertyDescriptor(window.HTMLTextAreaElement.prototype, 'value')?.set;
+  if (nativeInputValueSetter) {
+    nativeInputValueSetter.call(element, '');
+
+    const ev2 = new Event('input', { bubbles: true });
+    element.dispatchEvent(ev2);
+  }
+};
+
 /**
  * Chat UI with just the messages and textarea.
  * Reused between floating desktop chats and fullscreen/mobile chats.
  */
 const Chat: React.FC<ChatInterface> = ({ chat, inputRef, className }) => {
+  const intl = useIntl();
+
   const { createChatMessage, acceptChat } = useChatActions(chat.id);
 
   const [content, setContent] = useState<string>('');
@@ -30,20 +54,19 @@ const Chat: React.FC<ChatInterface> = ({ chat, inputRef, className }) => {
   // const [isUploading, setIsUploading] = useState(false);
   // const [uploadProgress, setUploadProgress] = useState(0);
   // const [resetFileKey, setResetFileKey] = useState<number>(fileKeyGen());
-  const [hasErrorSubmittingMessage, setErrorSubmittingMessage] = useState<boolean>(false);
+  const [errorMessage, setErrorMessage] = useState<string>();
 
   const isSubmitDisabled = content.length === 0 && !attachment;
 
   const submitMessage = () => {
     createChatMessage.mutate({ chatId: chat.id, content }, {
       onSuccess: () => {
-        setErrorSubmittingMessage(false);
+        setErrorMessage(undefined);
       },
-      onError: (error, _variables, context: any) => {
-        console.log(context);
-
+      onError: (error: AxiosError<{ error: string }>, _variables, context) => {
+        const message = error.response?.data?.error;
+        setErrorMessage(message || intl.formatMessage(messages.failedToSend));
         setContent(context.prevContent as string);
-        setErrorSubmittingMessage(true);
       },
     });
 
@@ -51,6 +74,9 @@ const Chat: React.FC<ChatInterface> = ({ chat, inputRef, className }) => {
   };
 
   const clearState = () => {
+    if (inputRef?.current) {
+      clearNativeInputValue(inputRef.current);
+    }
     setContent('');
     setAttachment(undefined);
     // setIsUploading(false);
@@ -172,7 +198,7 @@ const Chat: React.FC<ChatInterface> = ({ chat, inputRef, className }) => {
         value={content}
         onChange={handleContentChange}
         onSubmit={sendMessage}
-        hasErrorSubmittingMessage={hasErrorSubmittingMessage}
+        errorMessage={errorMessage}
       />
     </Stack>
     //   {renderAttachment()}