diff --git a/gateway/platforms/signal.py b/gateway/platforms/signal.py
index 79ccb551b28bf..aa0614a0921cf 100644
--- a/gateway/platforms/signal.py
+++ b/gateway/platforms/signal.py
@@ -615,7 +615,7 @@ def _track_sent_timestamp(self, rpc_result) -> None:
         if ts:
             self._recent_sent_timestamps.add(ts)
             if len(self._recent_sent_timestamps) > self._max_recent_timestamps:
-                self._recent_sent_timestamps.pop()
+                self._recent_sent_timestamps.discard(min(self._recent_sent_timestamps))
 
     async def send_typing(self, chat_id: str, metadata=None) -> None:
         """Send a typing indicator."""