diff --git a/surfsense_backend/app/tasks/connector_indexers/bookstack_indexer.py b/surfsense_backend/app/tasks/connector_indexers/bookstack_indexer.py
index 74234a3b9..6471ffb00 100644
--- a/surfsense_backend/app/tasks/connector_indexers/bookstack_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/bookstack_indexer.py
@@ -6,6 +6,7 @@ Implements 2-phase document status updates for real-time UI feedback:
 - Phase 2: Process each page: pending → processing → ready/failed
 """
 
+import contextlib
 import time
 from collections.abc import Awaitable, Callable
 from datetime import datetime
@@ -432,10 +433,15 @@ async def index_bookstack_pages(
                 try:
                     document.status = DocumentStatus.failed(str(e))
                     document.updated_at = get_current_timestamp()
+                    # Commit now so the failed status survives a later rollback or
+                    # crash; otherwise the doc stays stuck in pending/processing.
+                    await session.commit()
                 except Exception as status_error:
                     logger.error(
                         f"Failed to update document status to failed: {status_error}"
                     )
+                    with contextlib.suppress(Exception):
+                        await session.rollback()
                 skipped_pages.append(
                     f"{item.get('page_name', 'Unknown')} (processing error)"
                 )