diff --git a/backend/open_webui/models/files.py b/backend/open_webui/models/files.py
index f734ea62d..937a11768 100644
--- a/backend/open_webui/models/files.py
+++ b/backend/open_webui/models/files.py
@@ -257,7 +257,7 @@ class FilesTable:
                 return None
 
     def update_file_hash_by_id(
-        self, id: str, hash: str, db: Optional[Session] = None
+        self, id: str, hash: Optional[str], db: Optional[Session] = None
     ) -> Optional[FileModel]:
         with get_db_context(db) as db:
             try:
diff --git a/backend/open_webui/routers/retrieval.py b/backend/open_webui/routers/retrieval.py
index 379cf4da0..246855368 100644
--- a/backend/open_webui/routers/retrieval.py
+++ b/backend/open_webui/routers/retrieval.py
@@ -1794,6 +1794,8 @@ def process_file(
                 {"status": "failed"},
                 db=db,
             )
+            # Clear the hash so the file can be re-uploaded after fixing the issue
+            Files.update_file_hash_by_id(file.id, None, db=db)
 
             if "No pandoc was found" in str(e):
                 raise HTTPException(
diff --git a/backend/open_webui/utils/middleware.py b/backend/open_webui/utils/middleware.py
index 15414aa00..07b5a4b5e 100644
--- a/backend/open_webui/utils/middleware.py
+++ b/backend/open_webui/utils/middleware.py
@@ -2721,6 +2721,26 @@ async def process_chat_response(
                                                             "arguments"
                                                         ] += delta_arguments
 
+                                        # Emit pending tool calls in real-time
+                                        if response_tool_calls:
+                                            pending_content_blocks = content_blocks + [
+                                                {
+                                                    "type": "tool_calls",
+                                                    "content": response_tool_calls,
+                                                    "pending": True,
+                                                }
+                                            ]
+                                            await event_emitter(
+                                                {
+                                                    "type": "chat:completion",
+                                                    "data": {
+                                                        "content": serialize_content_blocks(
+                                                            pending_content_blocks
+                                                        ),
+                                                    },
+                                                }
+                                            )
+
                                     image_urls = get_image_urls(
                                         delta.get("images", []), request, metadata, user
                                     )