diff --git a/server/imserver/player.cc b/server/imserver/player.cc
index 1631644..5726cfb 100644
--- a/server/imserver/player.cc
+++ b/server/imserver/player.cc
@@ -491,6 +491,9 @@ void Player::_SS_IM_FriendAgreeRequest(f8::MsgHdr& hdr, const ss::SS_IM_FriendAg
                 return;
             }
             QueryUserOnline({friendobj->base_data.account_id});
+        } else {
+            SyncHelper::Instance()->SyncDeleteFriend(this,
+                                                     msg.context().user_info().base_data().account_id());
         }
     }
     RemoveHandledApply();
@@ -1022,6 +1025,7 @@ void Player::OnFriendAgreeEvent(Event& event)
         return;
     }
     if (!CanAddFriend(event.sender_id)) {
+        SyncHelper::Instance()->SyncDeleteFriend(this, event.sender_id);
         return;
     }
     Friend* friendobj = new Friend;