diff --git a/backend/video/views.py b/backend/video/views.py
index 7797056a..7a16faf0 100644
--- a/backend/video/views.py
+++ b/backend/video/views.py
@@ -335,7 +335,24 @@ class VideoStreamView(ApiBaseView):
         os.makedirs(cache_dir, exist_ok=True)
         cache_path = os.path.join(cache_dir, f"{video_id}.mp4")
 
-        if not os.path.exists(cache_path):
+        sentinel_path = cache_path + ".transcoding"
+
+        # Serve cached transcode immediately if available
+        if os.path.exists(cache_path):
+            response = FileResponse(open(cache_path, "rb"))
+            response["Content-Type"] = "video/mp4"
+            return response
+
+        # Guard against concurrent transcode of the same video
+        if os.path.exists(sentinel_path):
+            in_progress = Response({"status": "transcoding"}, status=202)
+            in_progress["Retry-After"] = "5"
+            return in_progress
+
+        # Run transcode; sentinel is removed regardless of outcome
+        try:
+            with open(sentinel_path, "w"):
+                pass  # create sentinel
             cmd = [
                 "ffmpeg",
                 "-y",
@@ -358,10 +375,15 @@ class VideoStreamView(ApiBaseView):
                 cache_path,
             ]
             subprocess.run(cmd, check=False)
+        finally:
+            try:
+                os.remove(sentinel_path)
+            except FileNotFoundError:
+                pass
 
         if not os.path.exists(cache_path):
             error = ErrorResponseSerializer({"error": "transcode failed"})
-            return Response(error.data, status=404)
+            return Response(error.data, status=500)
 
         response = FileResponse(open(cache_path, "rb"))
         response["Content-Type"] = "video/mp4"
diff --git a/frontend/src/components/VideoPlayer.tsx b/frontend/src/components/VideoPlayer.tsx
index 17b73cfa..9cd14a01 100644
--- a/frontend/src/components/VideoPlayer.tsx
+++ b/frontend/src/components/VideoPlayer.tsx
@@ -128,6 +128,19 @@ const VideoPlayer = ({
   setSeekToTimestamp,
 }: VideoPlayerProps) => {
   const videoRef = useRef<HTMLVideoElement | null>(null);
+  const [isTranscoding, setIsTranscoding] = useState(false);
+  const [retryKey, setRetryKey] = useState(0);
+
+  // If the video element errors (e.g. server returned 202 Transcoding),
+  // show a message and automatically retry after 5 seconds.
+  useEffect(() => {
+    if (!isTranscoding) return;
+    const timer = setTimeout(() => {
+      setIsTranscoding(false);
+      setRetryKey((k: number) => k + 1);
+    }, 5000);
+    return () => clearTimeout(timer);
+  }, [isTranscoding]);
 
   useEffect(() => {
     if (seekToTimestamp === undefined || !videoRef.current) {
@@ -413,9 +426,12 @@ const VideoPlayer = ({
         className={embed ? '' : `player-wrapper ${isTheaterMode ? 'theater-mode' : ''}`}
       >
         <div className={embed ? '' : `video-main ${isTheaterMode ? 'theater-mode' : ''}`}>
+          {isTranscoding && (
+            <p className="video-transcoding">Transcoding video for browser playback, retrying in 5 seconds…</p>
+          )}
           <video
             ref={videoRef}
-            key={`${getApiUrl()}${videoUrl}`}
+            key={`${getApiUrl()}${videoUrl}-${retryKey}`}
             poster={`${getApiUrl()}${videoThumbUrl}`}
             onVolumeChange={(videoTag: VideoTag) => {
               localStorage.setItem('playerVolume', videoTag.currentTarget.volume.toString());
@@ -445,6 +461,16 @@ const VideoPlayer = ({
               });
             }}
             onEnded={handleVideoEnd(videoId, watched)}
+            onError={async () => {
+              try {
+                const res = await fetch(`${getApiUrl()}${videoUrl}`, { method: 'HEAD' });
+                if (res.status === 202) {
+                  setIsTranscoding(true);
+                }
+              } catch {
+                // network error — ignore
+              }
+            }}
             onKeyDown={e => {
               if (e.key === 'ArrowLeft' || e.key === 'ArrowRight') {
                 e.preventDefault();