diff --git a/image_import_worker.py b/image_import_worker.py
index 552f826..274bb28 100644
--- a/image_import_worker.py
+++ b/image_import_worker.py
@@ -12,6 +12,9 @@ CHECK_INTERVAL = 10  # seconds
 
 app = create_app()
 
+from sqlalchemy.exc import OperationalError
+import time
+
 def monitor_and_import():
     with app.app_context():
         print("[Image Importer] Monitoring for trigger flag...")
@@ -19,43 +22,70 @@ def monitor_and_import():
         while True:
             if os.path.exists(TRIGGER_FLAG):
                 print("[Image Importer] Trigger flag found. Starting import...")
-                try:
-                    result = import_images_task(SOURCE_DIR, DEST_DIR)
-                    print(f"[Image Importer] {result}")
-                except Exception as e:
-                    print(f"[Image Importer] Error during import: {e}")
-                finally:
-                    try:
-                        os.remove(TRIGGER_FLAG)
-                        print("[Image Importer] Trigger flag cleared.")
-                    except Exception as e:
-                        print(f"[Image Importer] Failed to remove trigger flag: {e}")
+                max_retries = 3
+                attempt = 0
 
-            # Thumbnail generation Check
+                while attempt < max_retries:
+                    try:
+                        result = import_images_task(SOURCE_DIR, DEST_DIR)
+                        print(f"[Image Importer] {result}")
+                        break  # Exit retry loop if successful
+                    except OperationalError as e:
+                        attempt += 1
+                        print(f"[Image Importer] Database error during import (attempt {attempt}): {e}")
+                        if attempt >= max_retries:
+                            print("[Image Importer] Max retries reached. Import failed.")
+                        else:
+                            sleep_time = 2 ** attempt
+                            print(f"[Image Importer] Retrying in {sleep_time} seconds...")
+                            time.sleep(sleep_time)
+                    except Exception as e:
+                        print(f"[Image Importer] Unexpected error during import: {e}")
+                        break
+                    finally:
+                        try:
+                            os.remove(TRIGGER_FLAG)
+                            print("[Image Importer] Trigger flag cleared.")
+                        except Exception as e:
+                            print(f"[Image Importer] Failed to remove trigger flag: {e}")
+
+            # Thumbnail regeneration
             if os.path.exists(THUMBNAIL_FLAG):
                 print("[Image Importer] Thumbnail regeneration triggered.")
-                try:
-                    from app.models import ImageRecord
-                    from app.utils.image_importer import generate_thumbnail
+                max_retries = 3
+                attempt = 0
 
-                    for img in ImageRecord.query.all():
-                        try:
-                            generate_thumbnail(img.filepath, overwrite=True)
-                            print(f"[Thumbnail] Regenerated for {img.filename}")
-                        except Exception as e:
-                            print(f"[Thumbnail] Failed for {img.filename}: {e}")
-                        time.sleep(1)
-                except Exception as e:
-                    print(f"[Image Importer] Error during thumbnail regeneration: {e}")
-                finally:
+                while attempt < max_retries:
                     try:
-                        os.remove(THUMBNAIL_FLAG)
-                        print("[Image Importer] Thumbnail flag cleared.")
+                        from app.models import ImageRecord
+                        from app.utils.image_importer import generate_thumbnail
+
+                        for img in ImageRecord.query.all():
+                            try:
+                                generate_thumbnail(img.filepath, overwrite=True)
+                                print(f"[Thumbnail] Regenerated for {img.filename}")
+                            except Exception as e:
+                                print(f"[Thumbnail] Failed for {img.filename}: {e}")
+                        break  # Success
+                    except OperationalError as e:
+                        attempt += 1
+                        print(f"[Image Importer] Database error during thumbnail regen (attempt {attempt}): {e}")
+                        if attempt >= max_retries:
+                            print("[Image Importer] Max retries reached. Thumbnail regeneration failed.")
+                        else:
+                            sleep_time = 2 ** attempt
+                            print(f"[Image Importer] Retrying in {sleep_time} seconds...")
+                            time.sleep(sleep_time)
                     except Exception as e:
-                        print(f"[Image Importer] Failed to remove thumbnail flag: {e}")
+                        print(f"[Image Importer] Unexpected error during thumbnail regen: {e}")
+                        break
+                    finally:
+                        try:
+                            os.remove(THUMBNAIL_FLAG)
+                            print("[Image Importer] Thumbnail flag cleared.")
+                        except Exception as e:
+                            print(f"[Image Importer] Failed to remove thumbnail flag: {e}")
 
 
-            time.sleep(CHECK_INTERVAL)
-
 if __name__ == '__main__':
     monitor_and_import()