diff --git a/src/app/components/upload-card/UploadCardRenderer.tsx b/src/app/components/upload-card/UploadCardRenderer.tsx
index 281188d6f..c399d08c3 100644
--- a/src/app/components/upload-card/UploadCardRenderer.tsx
+++ b/src/app/components/upload-card/UploadCardRenderer.tsx
@@ -283,6 +283,12 @@ type UploadCardRendererProps = {
   setMetadata: (fileItem: TUploadItem, metadata: TUploadMetadata) => void;
   onRemove: (file: TUploadContent) => void;
   onComplete?: (upload: UploadSuccess) => void;
+  /** [Gitea #129] Focus the caption field on mount (single image into an empty composer). */
+  autoFocusCaption?: boolean;
+  /** Enter in the caption field: send the board (and any composer text). */
+  onCaptionSubmit?: () => void;
+  /** Escape in the caption field: hand focus back to the composer. */
+  onCaptionEscape?: () => void;
 };
 export function UploadCardRenderer({
   isEncrypted,
@@ -290,6 +296,9 @@ export function UploadCardRenderer({
   setMetadata,
   onRemove,
   onComplete,
+  autoFocusCaption,
+  onCaptionSubmit,
+  onCaptionEscape,
 }: UploadCardRendererProps) {
   const mx = useMatrixClient();
   const mediaConfig = useMediaConfig();
@@ -379,6 +388,16 @@ export function UploadCardRenderer({
               size="300"
               radii="300"
               style={{ marginTop: config.space.S200, width: '100%' }}
+              autoFocus={autoFocusCaption}
+              onKeyDown={(e: React.KeyboardEvent<HTMLInputElement>) => {
+                if (e.key === 'Enter' && !e.shiftKey && !e.nativeEvent.isComposing) {
+                  e.preventDefault();
+                  onCaptionSubmit?.();
+                } else if (e.key === 'Escape') {
+                  e.preventDefault();
+                  onCaptionEscape?.();
+                }
+              }}
             />
           )}
           <CompressionCheckbox fileItem={fileItem} metadata={metadata} setMetadata={setMetadata} />
diff --git a/src/app/features/room/RoomInput.tsx b/src/app/features/room/RoomInput.tsx
index 5e2bbd140..62a424115 100644
--- a/src/app/features/room/RoomInput.tsx
+++ b/src/app/features/room/RoomInput.tsx
@@ -158,6 +158,13 @@ const EmojiBoard = React.lazy(() =>
 );
 
 /** [Gitea #37] Debounce for persisting the composer draft while typing. */
+/** [Gitea #129] Same picked file, allowing for re-wrapped File objects. */
+const isAutoFocusTarget = (file: TUploadContent, target: File | undefined): boolean =>
+  !!target &&
+  file instanceof File &&
+  file.name === target.name &&
+  file.lastModified === target.lastModified;
+
 const DRAFT_PERSIST_DEBOUNCE_MS = 500;
 
 interface RoomInputProps {
@@ -253,6 +260,9 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
       selectedFiles.map((f) => f.file),
     );
     const uploadBoardHandlers = useRef<UploadBoardImperativeHandlers | undefined>(undefined);
+    // [Gitea #129] The file whose caption input should take focus once its card mounts.
+    // (Matched by name + mtime: the metadata strip and safeFile may re-wrap the File.)
+    const autoFocusCaptionRef = useRef<File | undefined>(undefined);
 
     const imagePackRooms: Room[] = useImagePackRooms(roomId, roomToParents);
 
@@ -379,12 +389,17 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
     const handleFiles = useCallback(
       async (files: File[]) => {
         setUploadBoard(true);
+        // [Gitea #129] One image into an empty composer: land in its caption
+        // field so "here's the bug" is one motion (Enter sends, Esc returns).
+        const focusCaption =
+          files.length === 1 && files[0].type.startsWith('image/') && isEmptyEditor(editor);
         setSelectedFiles({
           type: 'PUT',
           item: await filesToUploadItems(room, files, stripImageMetadata),
         });
+        if (focusCaption) autoFocusCaptionRef.current = files[0];
       },
-      [setSelectedFiles, room, stripImageMetadata],
+      [setSelectedFiles, room, stripImageMetadata, editor],
     );
     const pickFile = useFilePicker(handleFiles, true);
     const handleFilePaste = useFilePasteHandler(handleFiles);
@@ -1037,6 +1052,12 @@ export const RoomInput = forwardRef<HTMLDivElement, RoomInputProps>(
                         fileItem={fileItem}
                         setMetadata={handleFileMetadata}
                         onRemove={handleRemoveUpload}
+                        autoFocusCaption={isAutoFocusTarget(
+                          fileItem.originalFile,
+                          autoFocusCaptionRef.current,
+                        )}
+                        onCaptionSubmit={submit}
+                        onCaptionEscape={() => ReactEditor.focus(editor)}
                       />
                     ))}
                 </UploadBoardContent>