diff --git a/pyrogram/connection/transport/tcp/tcp.py b/pyrogram/connection/transport/tcp/tcp.py
index 168f06a5..08a435ce 100644
--- a/pyrogram/connection/transport/tcp/tcp.py
+++ b/pyrogram/connection/transport/tcp/tcp.py
@@ -101,6 +101,7 @@ class TCP:
                     await self.writer.drain()
             except Exception as e:
                 log.warning("Send exception: %s %s", type(e).__name__, e)
+                raise OSError(e)
 
     async def recv(self, length: int = 0):
         data = b""
diff --git a/pyrogram/session/session.py b/pyrogram/session/session.py
index e64ea793..6a7fc505 100644
--- a/pyrogram/session/session.py
+++ b/pyrogram/session/session.py
@@ -297,7 +297,11 @@ class Session:
             self.auth_key_id
         )
 
-        await self.connection.send(payload)
+        try:
+            await self.connection.send(payload)
+        except OSError as e:
+            self.results.pop(msg_id, None)
+            raise e
 
         if wait_response:
             try: