diff --git a/surfsense_backend/app/routes/documents_routes.py b/surfsense_backend/app/routes/documents_routes.py
index b20f8cd9c..226d511cc 100644
--- a/surfsense_backend/app/routes/documents_routes.py
+++ b/surfsense_backend/app/routes/documents_routes.py
@@ -178,9 +178,26 @@ async def create_documents_file_upload(
                     session, unique_identifier_hash
                 )
                 if existing:
-                    # Clean up temp file for duplicates
-                    os.unlink(temp_path)
-                    skipped_duplicates += 1
+                    if DocumentStatus.is_state(existing.status, DocumentStatus.READY):
+                        # True duplicate — content already indexed, skip
+                        os.unlink(temp_path)
+                        skipped_duplicates += 1
+                        continue
+
+                    # Existing document is stuck (failed/pending/processing)
+                    # Reset it to pending and re-dispatch for processing
+                    existing.status = DocumentStatus.pending()
+                    existing.content = "Processing..."
+                    existing.document_metadata = {
+                        **(existing.document_metadata or {}),
+                        "file_size": file_size,
+                        "upload_time": datetime.now().isoformat(),
+                    }
+                    existing.updated_at = get_current_timestamp()
+                    created_documents.append(existing)
+                    files_to_process.append(
+                        (existing, temp_path, file.filename or "unknown")
+                    )
                     continue
 
                 # Create pending document (visible immediately in UI via ElectricSQL)
diff --git a/surfsense_backend/app/tasks/celery_tasks/document_tasks.py b/surfsense_backend/app/tasks/celery_tasks/document_tasks.py
index 7fd866f1c..dfbfea432 100644
--- a/surfsense_backend/app/tasks/celery_tasks/document_tasks.py
+++ b/surfsense_backend/app/tasks/celery_tasks/document_tasks.py
@@ -413,7 +413,7 @@ def process_file_upload_task(
     if not os.path.exists(file_path):
         logger.error(
             f"[process_file_upload] File does not exist: {file_path}. "
-            "The temp file may have been cleaned up before the task ran."
+            "File may have been removed before syncing could start."
         )
         return
 
@@ -654,7 +654,7 @@ def process_file_upload_with_document_task(
     if not os.path.exists(temp_path):
         logger.error(
             f"[process_file_upload_with_document] File does not exist: {temp_path}. "
-            "The temp file may have been cleaned up before the task ran."
+            "File may have been removed before syncing could start."
         )
         # Mark document as failed since file is missing
         loop = asyncio.new_event_loop()
@@ -663,7 +663,7 @@ def process_file_upload_with_document_task(
             loop.run_until_complete(
                 _mark_document_failed(
                     document_id,
-                    "File not found - temp file may have been cleaned up",
+                    "File not found. Please re-upload the file.",
                 )
             )
         finally: