diff --git a/backend/open_webui/retrieval/loaders/youtube.py b/backend/open_webui/retrieval/loaders/youtube.py
index 61659d7bc1..a1ee8d1128 100644
--- a/backend/open_webui/retrieval/loaders/youtube.py
+++ b/backend/open_webui/retrieval/loaders/youtube.py
@@ -18,6 +18,32 @@ ALLOWED_NETLOCS = {
 }
 
 
+class YoutubeTranscriptError(Exception):
+    """A YouTube transcript could not be retrieved."""
+
+
+def _transcript_error_message(error: Exception, video_id: str) -> str:
+    name = type(error).__name__
+
+    if name in {'RequestBlocked', 'IpBlocked'}:
+        return (
+            f'YouTube blocked the transcript request for {video_id} from this server. '
+            'This usually means the server address is rate limited or belongs to a cloud '
+            'provider. A proxy for these requests can be configured under Admin Settings, '
+            'Web Search, Youtube Proxy URL.'
+        )
+    if name == 'TranscriptsDisabled':
+        return f'Transcripts are disabled for the YouTube video {video_id}.'
+    if name == 'AgeRestricted':
+        return f'The YouTube video {video_id} is age restricted, so its transcript cannot be retrieved.'
+    if name in {'VideoUnavailable', 'VideoUnplayable', 'InvalidVideoId'}:
+        return f'The YouTube video {video_id} is unavailable.'
+    if name == 'PoTokenRequired':
+        return f'YouTube requires additional verification to return the transcript for {video_id}.'
+
+    return f'Could not retrieve a transcript for the YouTube video {video_id}.'
+
+
 def _parse_video_id(url: str) -> Optional[str]:
     """Parse a YouTube URL and return the video ID if valid, otherwise None."""
     parsed_url = urlparse(url)
@@ -98,8 +124,8 @@ class YoutubeLoader:
         try:
             transcript_list = transcript_api.list(self.video_id)
         except Exception as e:
-            log.warning(f'Loading YouTube transcript failed: {e}')
-            return []
+            log.warning('Loading YouTube transcript failed: %s', e)
+            raise YoutubeTranscriptError(_transcript_error_message(e, self.video_id)) from e
 
         # Try each language in order of priority
         for lang in self.language:
@@ -139,14 +165,16 @@ class YoutubeLoader:
                 continue
             except Exception as e:
                 log.info("Error finding transcript for language '%s'", lang)
-                raise e
+                raise YoutubeTranscriptError(_transcript_error_message(e, self.video_id)) from e
 
         # If we get here, all languages failed
         languages_tried = ', '.join(self.language)
         log.warning(
             f'No transcript found for any of the specified languages: {languages_tried}. Verify if the video has transcripts, add more languages if needed.'
         )
-        raise NoTranscriptFound(self.video_id, self.language, list(transcript_list))
+        raise YoutubeTranscriptError(
+            f'No transcript found for the YouTube video {self.video_id} in these languages: {languages_tried}.'
+        )
 
     async def aload(self) -> Generator[Document, None, None]:
         """Asynchronously load YouTube transcripts into `Document` objects."""
diff --git a/backend/open_webui/routers/retrieval.py b/backend/open_webui/routers/retrieval.py
index 0128a5eb9a..4c55589b90 100644
--- a/backend/open_webui/routers/retrieval.py
+++ b/backend/open_webui/routers/retrieval.py
@@ -66,7 +66,7 @@ from open_webui.models.knowledge import Knowledges
 from open_webui.models.config import Config
 
 # Document loaders
-from open_webui.retrieval.loaders.youtube import YoutubeLoader
+from open_webui.retrieval.loaders.youtube import YoutubeLoader, YoutubeTranscriptError
 from open_webui.retrieval.utils import (
     build_loader_from_config,
     get_loader_config,
@@ -2336,8 +2336,25 @@ async def process_web(
     user=Depends(get_verified_user),
 ):
     config = await get_retrieval_config()
+
     try:
         content, docs = await get_content_from_url(request, form_data.url)
+    except HTTPException:
+        raise
+    except YoutubeTranscriptError as e:
+        log.warning('YouTube transcript unavailable for %s: %s', form_data.url, e)
+        raise HTTPException(
+            status_code=status.HTTP_400_BAD_REQUEST,
+            detail=str(e),
+        )
+    except Exception as e:
+        log.exception(e)
+        raise HTTPException(
+            status_code=status.HTTP_400_BAD_REQUEST,
+            detail=ERROR_MESSAGES.DEFAULT(e, f'Could not read content from {form_data.url}'),
+        )
+
+    try:
         log.debug('text_content: %s', content)
 
         if process: