diff --git a/backend/open_webui/events.py b/backend/open_webui/events.py
index 5b23231f41..81b8cc3968 100644
--- a/backend/open_webui/events.py
+++ b/backend/open_webui/events.py
@@ -411,6 +411,11 @@ class EventDefinitions(BaseModel):
         description='Retrieval content was processed.',
         message='Retrieval Content processed',
     )
+    RETRIEVAL_CONTENT_PROCESS_FAILED: EventDefinition = EventDefinition(
+        name='retrieval.content.process_failed',
+        description='Retrieval content processing failed.',
+        message='Retrieval Content process failed',
+    )
     RETRIEVAL_COLLECTION_DELETED: EventDefinition = EventDefinition(
         name='retrieval.collection.deleted',
         description='A retrieval collection was deleted.',
@@ -666,6 +671,7 @@ NOTIFICATION_EVENTS = (
     EVENTS.CHAT_FAILED.name,
     EVENTS.CHANNEL_MESSAGE.name,
     EVENTS.CALENDAR_ALERT.name,
+    EVENTS.RETRIEVAL_CONTENT_PROCESS_FAILED.name,
 )
 
 
diff --git a/backend/open_webui/routers/retrieval.py b/backend/open_webui/routers/retrieval.py
index 464a2b233b..d81e1e4e2c 100644
--- a/backend/open_webui/routers/retrieval.py
+++ b/backend/open_webui/routers/retrieval.py
@@ -1998,7 +1998,7 @@ async def process_file(
             hash = calculate_sha256_string(text_content)
 
             if config.BYPASS_EMBEDDING_AND_RETRIEVAL:
-                await Files.update_file_data_by_id(file.id, {'status': 'completed'}, db=db)
+                await Files.update_file_data_by_id(file.id, {'status': 'completed', 'error': None}, db=db)
                 await Files.update_file_hash_by_id(file.id, hash, db=db)
                 await publish_event(
                     request,
@@ -2057,7 +2057,7 @@ async def process_file(
 
                             await Files.update_file_data_by_id(
                                 file.id,
-                                {'status': 'completed'},
+                                {'status': 'completed', 'error': None},
                                 db=session,
                             )
                             await Files.update_file_hash_by_id(file.id, hash, db=session)
@@ -2087,12 +2087,25 @@ async def process_file(
             async with get_async_db() as session:
                 await Files.update_file_data_by_id(
                     file.id,
-                    {'status': 'failed'},
+                    {'status': 'failed', 'error': str(e)},
                     db=session,
                 )
                 # Clear the hash so the file can be re-uploaded after fixing the issue
                 await Files.update_file_hash_by_id(file.id, None, db=session)
 
+            await publish_event(
+                request,
+                EVENTS.RETRIEVAL_CONTENT_PROCESS_FAILED,
+                actor=user,
+                subject_id=file.id,
+                subject_type='file',
+                data={
+                    'collection_name': collection_name,
+                    'filename': file.filename,
+                    'message': f'{file.filename}: {e}',
+                },
+            )
+
             if 'No pandoc was found' in str(e):
                 raise HTTPException(
                     status_code=status.HTTP_400_BAD_REQUEST,