diff --git a/routes/__pycache__/room_files.cpython-313.pyc b/routes/__pycache__/room_files.cpython-313.pyc
index e94e7fd..0562f90 100644
Binary files a/routes/__pycache__/room_files.cpython-313.pyc and b/routes/__pycache__/room_files.cpython-313.pyc differ
diff --git a/routes/room_files.py b/routes/room_files.py
index 5bd7da9..fd3065c 100644
--- a/routes/room_files.py
+++ b/routes/room_files.py
@@ -676,7 +676,18 @@ def delete_permanent(room_id):
                 if rf.type == 'file':
                     os.remove(file_path)
                 elif rf.type == 'folder':
+                    # For folders, we need to delete all contents recursively
                     shutil.rmtree(file_path)
+                    
+                    # Also delete all database records for files and subfolders
+                    folder_path = os.path.join(rf.path, rf.name) if rf.path else rf.name
+                    contained_items = RoomFile.query.filter(
+                        RoomFile.room_id == room_id,
+                        RoomFile.path.like(f"{folder_path}%")
+                    ).all()
+                    
+                    for item in contained_items:
+                        db.session.delete(item)
         except Exception as e:
             print(f"Error deleting {rf.type} from storage: {e}")