diff --git a/app/soapbox/components/ui/progress-bar/progress-bar.tsx b/app/soapbox/components/ui/progress-bar/progress-bar.tsx
index c0161ae34..0507045e4 100644
--- a/app/soapbox/components/ui/progress-bar/progress-bar.tsx
+++ b/app/soapbox/components/ui/progress-bar/progress-bar.tsx
@@ -1,13 +1,32 @@
+import clsx from 'clsx';
 import React from 'react';
+import { spring } from 'react-motion';
+
+import Motion from 'soapbox/features/ui/util/optional-motion';
 
 interface IProgressBar {
-  progress: number,
+  /** Number between 0 and 1 to represent the percentage complete. */
+  progress: number
+  /** Height of the progress bar. */
+  size?: 'sm' | 'md'
 }
 
 /** A horizontal meter filled to the given percentage. */
-const ProgressBar: React.FC<IProgressBar> = ({ progress }) => (
-  <div className='h-2.5 w-full overflow-hidden rounded-full bg-gray-300 dark:bg-primary-800'>
-    <div className='h-full bg-secondary-500' style={{ width: `${Math.floor(progress * 100)}%` }} />
+const ProgressBar: React.FC<IProgressBar> = ({ progress, size = 'md' }) => (
+  <div
+    className={clsx('h-2.5 w-full overflow-hidden rounded-lg bg-gray-300 dark:bg-primary-800', {
+      'h-2.5': size === 'md',
+      'h-[6px]': size === 'sm',
+    })}
+  >
+    <Motion defaultStyle={{ width: 0 }} style={{ width: spring(progress * 100) }}>
+      {({ width }) => (
+        <div
+          className='h-full bg-secondary-500'
+          style={{ width: `${width}%` }}
+        />
+      )}
+    </Motion>
   </div>
 );
 
diff --git a/app/soapbox/components/ui/textarea/textarea.tsx b/app/soapbox/components/ui/textarea/textarea.tsx
index 4b2274a21..1b1081ce4 100644
--- a/app/soapbox/components/ui/textarea/textarea.tsx
+++ b/app/soapbox/components/ui/textarea/textarea.tsx
@@ -26,6 +26,8 @@ interface ITextarea extends Pick<React.TextareaHTMLAttributes<HTMLTextAreaElemen
   hasError?: boolean,
   /** Whether or not you can resize the teztarea */
   isResizeable?: boolean,
+  /** Textarea theme. */
+  theme?: 'default' | 'transparent',
 }
 
 /** Textarea with custom styles. */
@@ -37,6 +39,7 @@ const Textarea = React.forwardRef(({
   autoGrow = false,
   maxRows = 10,
   minRows = 1,
+  theme = 'default',
   ...props
 }: ITextarea, ref: React.ForwardedRef<HTMLTextAreaElement>) => {
   const [rows, setRows] = useState<number>(autoGrow ? 1 : 4);
@@ -72,9 +75,10 @@ const Textarea = React.forwardRef(({
       ref={ref}
       rows={rows}
       onChange={handleChange}
-      className={clsx({
-        'bg-white dark:bg-transparent shadow-sm block w-full sm:text-sm rounded-md text-gray-900 dark:text-gray-100 placeholder:text-gray-600 dark:placeholder:text-gray-600 border-gray-400 dark:border-gray-800 dark:ring-1 dark:ring-gray-800 focus:ring-primary-500 focus:border-primary-500 dark:focus:ring-primary-500 dark:focus:border-primary-500':
-          true,
+      className={clsx('block w-full rounded-md text-gray-900 placeholder:text-gray-600 dark:text-gray-100 dark:placeholder:text-gray-600 sm:text-sm', {
+        'bg-white dark:bg-transparent shadow-sm border-gray-400 dark:border-gray-800 dark:ring-1 dark:ring-gray-800 focus:ring-primary-500 focus:border-primary-500 dark:focus:ring-primary-500 dark:focus:border-primary-500':
+          theme === 'default',
+        'bg-transparent border-0 focus:border-0 focus:ring-0': theme === 'transparent',
         'font-mono': isCodeEditor,
         'text-red-600 border-red-600': hasError,
         'resize-none': !isResizeable,
diff --git a/app/soapbox/components/upload-progress.tsx b/app/soapbox/components/upload-progress.tsx
index 5cbb4e1b3..f434c4673 100644
--- a/app/soapbox/components/upload-progress.tsx
+++ b/app/soapbox/components/upload-progress.tsx
@@ -1,13 +1,11 @@
 import React from 'react';
 import { FormattedMessage } from 'react-intl';
-import { spring } from 'react-motion';
 
-import { HStack, Icon, Stack, Text } from 'soapbox/components/ui';
-import Motion from 'soapbox/features/ui/util/optional-motion';
+import { HStack, Icon, ProgressBar, Stack, Text } from 'soapbox/components/ui';
 
 interface IUploadProgress {
-  /** Number between 0 and 1 to represent the percentage complete. */
-  progress: number,
+  /** Number between 0 and 100 to represent the percentage complete. */
+  progress: number
 }
 
 /** Displays a progress bar for uploading files. */
@@ -24,16 +22,7 @@ const UploadProgress: React.FC<IUploadProgress> = ({ progress }) => {
           <FormattedMessage id='upload_progress.label' defaultMessage='Uploading…' />
         </Text>
 
-        <div className='relative h-1.5 w-full rounded-lg bg-gray-200'>
-          <Motion defaultStyle={{ width: 0 }} style={{ width: spring(progress) }}>
-            {({ width }) =>
-              (<div
-                className='absolute left-0 top-0 h-1.5 rounded-lg bg-primary-600'
-                style={{ width: `${width}%` }}
-              />)
-            }
-          </Motion>
-        </div>
+        <ProgressBar progress={progress / 100} size='sm' />
       </Stack>
     </HStack>
   );
diff --git a/app/soapbox/features/chats/components/chat-composer.tsx b/app/soapbox/features/chats/components/chat-composer.tsx
index a703d772f..165e7ce9d 100644
--- a/app/soapbox/features/chats/components/chat-composer.tsx
+++ b/app/soapbox/features/chats/components/chat-composer.tsx
@@ -3,13 +3,16 @@ import { defineMessages, IntlShape, useIntl } from 'react-intl';
 
 import { unblockAccount } from 'soapbox/actions/accounts';
 import { openModal } from 'soapbox/actions/modals';
-import { Button, Combobox, ComboboxInput, ComboboxList, ComboboxOption, ComboboxPopover, HStack, IconButton, Stack, Text, Textarea } from 'soapbox/components/ui';
+import { Button, Combobox, ComboboxInput, ComboboxList, ComboboxOption, ComboboxPopover, HStack, IconButton, Stack, Text } from 'soapbox/components/ui';
 import { useChatContext } from 'soapbox/contexts/chat-context';
 import UploadButton from 'soapbox/features/compose/components/upload-button';
 import { search as emojiSearch } from 'soapbox/features/emoji/emoji-mart-search-light';
 import { useAppDispatch, useAppSelector, useFeatures } from 'soapbox/hooks';
+import { Attachment } from 'soapbox/types/entities';
 import { textAtCursorMatchesToken } from 'soapbox/utils/suggestions';
 
+import ChatTextarea from './chat-textarea';
+
 const messages = defineMessages({
   placeholder: { id: 'chat.input.placeholder', defaultMessage: 'Type a message' },
   send: { id: 'chat.actions.send', defaultMessage: 'Send' },
@@ -39,7 +42,10 @@ interface IChatComposer extends Pick<React.TextareaHTMLAttributes<HTMLTextAreaEl
   errorMessage: string | undefined
   onSelectFile: (files: FileList, intl: IntlShape) => void
   resetFileKey: number | null
-  hasAttachment?: boolean
+  attachments?: Attachment[]
+  onDeleteAttachment?: () => void
+  isUploading?: boolean
+  uploadProgress?: number
 }
 
 /** Textarea input for chats. */
@@ -53,7 +59,10 @@ const ChatComposer = React.forwardRef<HTMLTextAreaElement | null, IChatComposer>
   onSelectFile,
   resetFileKey,
   onPaste,
-  hasAttachment,
+  attachments = [],
+  onDeleteAttachment,
+  isUploading,
+  uploadProgress,
 }, ref) => {
   const intl = useIntl();
   const dispatch = useAppDispatch();
@@ -68,6 +77,7 @@ const ChatComposer = React.forwardRef<HTMLTextAreaElement | null, IChatComposer>
   const [suggestions, setSuggestions] = useState<Suggestion>(initialSuggestionState);
   const isSuggestionsAvailable = suggestions.list.length > 0;
 
+  const hasAttachment = attachments.length > 0;
   const isOverCharacterLimit = maxCharacterCount && value?.length > maxCharacterCount;
   const isSubmitDisabled = disabled || isOverCharacterLimit || (value.length === 0 && !hasAttachment);
 
@@ -167,12 +177,9 @@ const ChatComposer = React.forwardRef<HTMLTextAreaElement | null, IChatComposer>
         )}
 
         <Stack grow>
-          <Combobox
-            aria-labelledby='demo'
-            onSelect={onSelectComboboxOption}
-          >
+          <Combobox onSelect={onSelectComboboxOption}>
             <ComboboxInput
-              as={Textarea}
+              as={ChatTextarea}
               autoFocus
               ref={ref}
               placeholder={intl.formatMessage(messages.placeholder)}
@@ -184,6 +191,10 @@ const ChatComposer = React.forwardRef<HTMLTextAreaElement | null, IChatComposer>
               autoGrow
               maxRows={5}
               disabled={disabled}
+              attachments={attachments}
+              onDeleteAttachment={onDeleteAttachment}
+              isUploading={isUploading}
+              uploadProgress={uploadProgress}
             />
             {isSuggestionsAvailable ? (
               <ComboboxPopover>
diff --git a/app/soapbox/features/chats/components/chat-message-list.tsx b/app/soapbox/features/chats/components/chat-message-list.tsx
index 1a2b1bd65..b1d9a0491 100644
--- a/app/soapbox/features/chats/components/chat-message-list.tsx
+++ b/app/soapbox/features/chats/components/chat-message-list.tsx
@@ -195,13 +195,12 @@ const ChatMessageList: React.FC<IChatMessageList> = ({ chat }) => {
   };
 
   const maybeRenderMedia = (chatMessage: ChatMessageEntity) => {
-    const { attachment } = chatMessage;
-    if (!attachment) return null;
+    if (!chatMessage.media_attachments.size) return null;
     return (
       <Bundle fetchComponent={MediaGallery}>
         {(Component: any) => (
           <Component
-            media={ImmutableList([attachment])}
+            media={chatMessage.media_attachments}
             onOpenMedia={onOpenMedia}
             visible
           />
@@ -316,7 +315,7 @@ const ChatMessageList: React.FC<IChatMessageList> = ({ chat }) => {
               space={0.5}
               className={clsx({
                 'max-w-[85%]': true,
-                'flex-1': chatMessage.attachment,
+                'flex-1': !!chatMessage.media_attachments.size,
                 'order-2': isMyMessage,
                 'order-1': !isMyMessage,
               })}
@@ -331,8 +330,8 @@ const ChatMessageList: React.FC<IChatMessageList> = ({ chat }) => {
                     className={
                       clsx({
                         'text-ellipsis break-words relative rounded-md py-2 px-3 max-w-full space-y-2 [&_.mention]:underline': true,
-                        'rounded-tr-sm': chatMessage.attachment && isMyMessage,
-                        'rounded-tl-sm': chatMessage.attachment && !isMyMessage,
+                        'rounded-tr-sm': (!!chatMessage.media_attachments.size) && isMyMessage,
+                        'rounded-tl-sm': (!!chatMessage.media_attachments.size) && !isMyMessage,
                         '[&_.mention]:text-primary-600 dark:[&_.mention]:text-accent-blue': !isMyMessage,
                         '[&_.mention]:text-white dark:[&_.mention]:white': isMyMessage,
                         'bg-primary-500 text-white': isMyMessage,
diff --git a/app/soapbox/features/chats/components/chat-pending-upload.tsx b/app/soapbox/features/chats/components/chat-pending-upload.tsx
new file mode 100644
index 000000000..373d548ce
--- /dev/null
+++ b/app/soapbox/features/chats/components/chat-pending-upload.tsx
@@ -0,0 +1,18 @@
+import React from 'react';
+
+import { ProgressBar } from 'soapbox/components/ui';
+
+interface IChatPendingUpload {
+  progress: number
+}
+
+/** Displays a loading thumbnail for an upload in the chat composer. */
+const ChatPendingUpload: React.FC<IChatPendingUpload> = ({ progress }) => {
+  return (
+    <div className='relative isolate inline-flex h-24 w-24 items-center justify-center overflow-hidden rounded-lg bg-gray-200 p-4 dark:bg-primary-900'>
+      <ProgressBar progress={progress} size='sm' />
+    </div>
+  );
+};
+
+export default ChatPendingUpload;
\ No newline at end of file
diff --git a/app/soapbox/features/chats/components/chat-textarea.tsx b/app/soapbox/features/chats/components/chat-textarea.tsx
new file mode 100644
index 000000000..22b0877e9
--- /dev/null
+++ b/app/soapbox/features/chats/components/chat-textarea.tsx
@@ -0,0 +1,58 @@
+import React from 'react';
+
+import { Textarea } from 'soapbox/components/ui';
+import { Attachment } from 'soapbox/types/entities';
+
+import ChatPendingUpload from './chat-pending-upload';
+import ChatUpload from './chat-upload';
+
+interface IChatTextarea extends React.ComponentProps<typeof Textarea> {
+  attachments?: Attachment[]
+  onDeleteAttachment?: () => void
+  isUploading?: boolean
+  uploadProgress?: number
+}
+
+/** Custom textarea for chats. */
+const ChatTextarea: React.FC<IChatTextarea> = ({
+  attachments,
+  onDeleteAttachment,
+  isUploading = false,
+  uploadProgress = 0,
+  ...rest
+}) => {
+  return (
+    <div className={`
+      block
+      w-full
+      rounded-md border border-gray-400
+      bg-white text-gray-900
+      shadow-sm placeholder:text-gray-600
+      focus-within:border-primary-500
+      focus-within:ring-1 focus-within:ring-primary-500 dark:border-gray-800 dark:bg-gray-800
+      dark:text-gray-100 dark:ring-1 dark:ring-gray-800 dark:placeholder:text-gray-600 dark:focus-within:border-primary-500
+      dark:focus-within:ring-primary-500 sm:text-sm
+    `}
+    >
+      {(!!attachments?.length || isUploading) && (
+        <div className='flex p-3 pb-0'>
+          {isUploading && (
+            <ChatPendingUpload progress={uploadProgress} />
+          )}
+
+          {attachments?.map(attachment => (
+            <ChatUpload
+              key={attachment.id}
+              attachment={attachment}
+              onDelete={onDeleteAttachment}
+            />
+          ))}
+        </div>
+      )}
+
+      <Textarea theme='transparent' {...rest} />
+    </div>
+  );
+};
+
+export default ChatTextarea;
\ No newline at end of file
diff --git a/app/soapbox/features/chats/components/chat-upload-preview.tsx b/app/soapbox/features/chats/components/chat-upload-preview.tsx
new file mode 100644
index 000000000..14864fd91
--- /dev/null
+++ b/app/soapbox/features/chats/components/chat-upload-preview.tsx
@@ -0,0 +1,55 @@
+import React from 'react';
+
+import { Icon } from 'soapbox/components/ui';
+import { MIMETYPE_ICONS } from 'soapbox/components/upload';
+
+import type { Attachment } from 'soapbox/types/entities';
+
+const defaultIcon = require('@tabler/icons/paperclip.svg');
+
+interface IChatUploadPreview {
+  className?: string
+  attachment: Attachment
+}
+
+/**
+ * Displays a generic preview for an upload depending on its media type.
+ * It fills its container and is expected to be sized by its parent.
+ */
+const ChatUploadPreview: React.FC<IChatUploadPreview> = ({ className, attachment }) => {
+  const mimeType = attachment.pleroma.get('mime_type') as string | undefined;
+
+  switch (attachment.type) {
+    case 'image':
+      return (
+        <img
+          className='pointer-events-none h-full w-full object-cover'
+          src={attachment.preview_url}
+          alt=''
+        />
+      );
+    case 'video':
+      return (
+        <video
+          className='pointer-events-none h-full w-full object-cover'
+          src={attachment.preview_url}
+          autoPlay
+          playsInline
+          controls={false}
+          muted
+          loop
+        />
+      );
+    default:
+      return (
+        <div className='pointer-events-none flex h-full w-full items-center justify-center'>
+          <Icon
+            className='mx-auto my-12 h-16 w-16 text-gray-800 dark:text-gray-200'
+            src={MIMETYPE_ICONS[mimeType || ''] || defaultIcon}
+          />
+        </div>
+      );
+  }
+};
+
+export default ChatUploadPreview;
\ No newline at end of file
diff --git a/app/soapbox/features/chats/components/chat-upload.tsx b/app/soapbox/features/chats/components/chat-upload.tsx
new file mode 100644
index 000000000..9aa969e3a
--- /dev/null
+++ b/app/soapbox/features/chats/components/chat-upload.tsx
@@ -0,0 +1,66 @@
+import clsx from 'clsx';
+import { List as ImmutableList } from 'immutable';
+import React from 'react';
+
+import { openModal } from 'soapbox/actions/modals';
+import Blurhash from 'soapbox/components/blurhash';
+import { Icon } from 'soapbox/components/ui';
+import { useAppDispatch } from 'soapbox/hooks';
+
+import ChatUploadPreview from './chat-upload-preview';
+
+import type { Attachment } from 'soapbox/types/entities';
+
+interface IChatUpload {
+  attachment: Attachment,
+  onDelete?(): void,
+}
+
+/** An attachment uploaded to the chat composer, before sending. */
+const ChatUpload: React.FC<IChatUpload> = ({ attachment, onDelete }) => {
+  const dispatch = useAppDispatch();
+  const clickable = attachment.type !== 'unknown';
+
+  const handleOpenModal = () => {
+    dispatch(openModal('MEDIA', { media: ImmutableList.of(attachment), index: 0 }));
+  };
+
+  return (
+    <div className='relative isolate inline-block h-24 w-24 overflow-hidden rounded-lg bg-gray-200 dark:bg-primary-900'>
+      <Blurhash hash={attachment.blurhash} className='absolute inset-0 -z-10 h-full w-full' />
+
+      <div className='absolute right-[6px] top-[6px]'>
+        <RemoveButton onClick={onDelete} />
+      </div>
+
+      <button
+        onClick={clickable ? handleOpenModal : undefined}
+        className={clsx('h-full w-full', { 'cursor-zoom-in': clickable, 'cursor-default': !clickable })}
+      >
+        <ChatUploadPreview attachment={attachment} />
+      </button>
+    </div>
+  );
+};
+
+interface IRemoveButton {
+  onClick?: React.MouseEventHandler<HTMLButtonElement>
+}
+
+/** Floating button to remove an attachment. */
+const RemoveButton: React.FC<IRemoveButton> = ({ onClick }) => {
+  return (
+    <button
+      type='button'
+      onClick={onClick}
+      className='flex h-5 w-5 items-center justify-center rounded-full bg-secondary-500 p-1'
+    >
+      <Icon
+        className='h-3 w-3 text-white'
+        src={require('@tabler/icons/x.svg')}
+      />
+    </button>
+  );
+};
+
+export default ChatUpload;
\ No newline at end of file
diff --git a/app/soapbox/features/chats/components/chat.tsx b/app/soapbox/features/chats/components/chat.tsx
index c04032666..55b0cf2cb 100644
--- a/app/soapbox/features/chats/components/chat.tsx
+++ b/app/soapbox/features/chats/components/chat.tsx
@@ -5,8 +5,6 @@ import { defineMessages, useIntl } from 'react-intl';
 
 import { uploadMedia } from 'soapbox/actions/media';
 import { Stack } from 'soapbox/components/ui';
-import Upload from 'soapbox/components/upload';
-import UploadProgress from 'soapbox/components/upload-progress';
 import { useAppDispatch } from 'soapbox/hooks';
 import { normalizeAttachment } from 'soapbox/normalizers';
 import { IChat, useChatActions } from 'soapbox/queries/chats';
@@ -164,22 +162,6 @@ const Chat: React.FC<ChatInterface> = ({ chat, inputRef, className }) => {
         <ChatMessageList chat={chat} />
       </div>
 
-      {attachment && (
-        <div className='relative h-48'>
-          <Upload
-            media={attachment}
-            onDelete={handleRemoveFile}
-            withPreview
-          />
-        </div>
-      )}
-
-      {isUploading && (
-        <div className='p-4'>
-          <UploadProgress progress={uploadProgress * 100} />
-        </div>
-      )}
-
       <ChatComposer
         ref={inputRef}
         onKeyDown={handleKeyDown}
@@ -190,7 +172,10 @@ const Chat: React.FC<ChatInterface> = ({ chat, inputRef, className }) => {
         onSelectFile={handleFiles}
         resetFileKey={resetFileKey}
         onPaste={handlePaste}
-        hasAttachment={!!attachment}
+        attachments={attachment ? [attachment] : []}
+        onDeleteAttachment={handleRemoveFile}
+        isUploading={isUploading}
+        uploadProgress={uploadProgress}
       />
     </Stack>
   );
diff --git a/app/soapbox/normalizers/__tests__/chat-message.test.ts b/app/soapbox/normalizers/__tests__/chat-message.test.ts
new file mode 100644
index 000000000..0ada7b8b3
--- /dev/null
+++ b/app/soapbox/normalizers/__tests__/chat-message.test.ts
@@ -0,0 +1,23 @@
+import { Record as ImmutableRecord } from 'immutable';
+
+import { normalizeAttachment } from '../attachment';
+import { normalizeChatMessage } from '../chat-message';
+
+describe('normalizeChatMessage()', () => {
+  it('upgrades attachment to media_attachments', () => {
+    const message = {
+      id: 'abc',
+      attachment: normalizeAttachment({
+        id: 'def',
+        url: 'https://gleasonator.com/favicon.png',
+      }),
+    };
+
+    const result = normalizeChatMessage(message);
+
+    expect(ImmutableRecord.isRecord(result)).toBe(true);
+    expect(result.id).toEqual('abc');
+    expect(result.media_attachments.first()?.id).toEqual('def');
+    expect(result.media_attachments.first()?.preview_url).toEqual('https://gleasonator.com/favicon.png');
+  });
+});
diff --git a/app/soapbox/normalizers/chat-message.ts b/app/soapbox/normalizers/chat-message.ts
index af67f351e..e928eeaaf 100644
--- a/app/soapbox/normalizers/chat-message.ts
+++ b/app/soapbox/normalizers/chat-message.ts
@@ -11,7 +11,7 @@ import type { Attachment, Card, Emoji } from 'soapbox/types/entities';
 
 export const ChatMessageRecord = ImmutableRecord({
   account_id: '',
-  attachment: null as Attachment | null,
+  media_attachments: ImmutableList<Attachment>(),
   card: null as Card | null,
   chat_id: '',
   content: '',
@@ -24,12 +24,15 @@ export const ChatMessageRecord = ImmutableRecord({
 });
 
 const normalizeMedia = (status: ImmutableMap<string, any>) => {
+  const attachments = status.get('media_attachments');
   const attachment = status.get('attachment');
 
-  if (attachment) {
-    return status.set('attachment', normalizeAttachment(attachment));
+  if (attachments) {
+    return status.set('media_attachments', ImmutableList(attachments.map(normalizeAttachment)));
+  } else if (attachment) {
+    return status.set('media_attachments', ImmutableList([normalizeAttachment(attachment)]));
   } else {
-    return status;
+    return status.set('media_attachments', ImmutableList());
   }
 };
 
diff --git a/app/soapbox/queries/chats.ts b/app/soapbox/queries/chats.ts
index ace2722a8..28fb403b3 100644
--- a/app/soapbox/queries/chats.ts
+++ b/app/soapbox/queries/chats.ts
@@ -235,7 +235,7 @@ const useChatActions = (chatId: string) => {
   const createChatMessage = useMutation(
     (
       {  chatId, content, mediaId }: { chatId: string, content: string, mediaId?: string },
-    ) => api.post<IChatMessage>(`/api/v1/pleroma/chats/${chatId}/messages`, { content, media_id: mediaId }),
+    ) => api.post<IChatMessage>(`/api/v1/pleroma/chats/${chatId}/messages`, { content, media_id: mediaId, media_ids: [mediaId] }),
     {
       retry: false,
       onMutate: async (variables) => {