diff --git a/src/steps/crm/akte/akte_sync_event_step.py b/src/steps/crm/akte/akte_sync_event_step.py
index dc90629..1d0549b 100644
--- a/src/steps/crm/akte/akte_sync_event_step.py
+++ b/src/steps/crm/akte/akte_sync_event_step.py
@@ -684,11 +684,17 @@ async def _run_ragflow_sync(
                 ctx.logger.info(
                     f"     ⏭️  Nicht unterstützter Dateityp ({mime_type}) – übersprungen"
                 )
-                if not ragflow_doc_id:
-                    await espocrm.update_entity('CDokumente', doc_id, {
-                        'aiSyncStatus': 'unsupported',
-                        'aiLastSync': datetime.now().strftime('%Y-%m-%d %H:%M:%S'),
-                    })
+                # If doc was previously uploaded to RAGflow (e.g. type changed), remove it
+                if ragflow_doc_id:
+                    try:
+                        await ragflow.remove_document(dataset_id, ragflow_doc_id)
+                        ctx.logger.info(f"     🗑️  Aus RAGflow entfernt (nicht unterstützt): {ragflow_doc_id}")
+                    except Exception as e:
+                        ctx.logger.warn(f"     ⚠️  RAGflow-Löschung fehlgeschlagen: {e}")
+                await espocrm.update_entity('CDokumente', doc_id, {
+                    'aiSyncStatus': 'unsupported',
+                    'aiLastSync': datetime.now().strftime('%Y-%m-%d %H:%M:%S'),
+                })
                 skipped += 1
                 continue