diff --git a/app/device_manager.py b/app/device_manager.py
index dca9c8b..83e3cc5 100644
--- a/app/device_manager.py
+++ b/app/device_manager.py
@@ -547,6 +547,18 @@ class DeviceManager:
                     'route_type': data.get('route_type', ''),
                 }, namespace='/chat')
 
+            # Cancel retry task if ACK confirms delivery for a pending DM
+            if dm_id:
+                task = self._retry_tasks.get(dm_id)
+                if task and not task.done():
+                    task.cancel()
+                    logger.info(f"Cancelled retry task for dm_id={dm_id} (ACK received)")
+                # Cleanup all pending acks for this DM
+                stale = [k for k, v in self._pending_acks.items() if v == dm_id]
+                for k in stale:
+                    self._pending_acks.pop(k, None)
+                self._retry_tasks.pop(dm_id, None)
+
         except Exception as e:
             logger.error(f"Error handling ACK: {e}")
 
@@ -655,6 +667,15 @@ class DeviceManager:
                                 'dm_id': dm_id,
                                 'route_type': 'PATH_FLOOD',
                             }, namespace='/chat')
+                        # Cancel retry task — delivery already confirmed
+                        task = self._retry_tasks.get(dm_id)
+                        if task and not task.done():
+                            task.cancel()
+                            logger.info(f"Cancelled retry task for dm_id={dm_id} (PATH confirmed)")
+                        stale_acks = [k for k, v in self._pending_acks.items() if v == dm_id]
+                        for k in stale_acks:
+                            self._pending_acks.pop(k, None)
+                        self._retry_tasks.pop(dm_id, None)
                     break  # Only confirm the most recent pending DM to this contact
 
         except Exception as e:
@@ -1053,11 +1074,14 @@ class DeviceManager:
                     return
 
         logger.warning(f"DM retry exhausted ({max_attempts} attempts) for dm_id={dm_id}")
-        # Cleanup stale pending acks for this DM
-        stale = [k for k, v in self._pending_acks.items() if v == dm_id]
-        for k in stale:
-            self._pending_acks.pop(k, None)
+        # Keep pending acks for grace period so late ACKs can still be matched
         self._retry_tasks.pop(dm_id, None)
+        await asyncio.sleep(60)
+        stale = [k for k, v in self._pending_acks.items() if v == dm_id]
+        if stale:
+            for k in stale:
+                self._pending_acks.pop(k, None)
+            logger.debug(f"Grace period expired, cleaned {len(stale)} pending acks for dm_id={dm_id}")
 
     def _confirm_delivery(self, dm_id: int, ack_code: str, ack_event):
         """Store ACK and notify frontend."""