diff --git a/listener.c b/listener.c
index a78ca0d6..d21e8dbe 100644
--- a/listener.c
+++ b/listener.c
@@ -741,6 +741,10 @@ iocp_listener_disable_impl(struct evconnlistener *lev, int shutdown)
 		}
 		LeaveCriticalSection(&as->lock);
 	}
+
+	if (shutdown && lev->flags & LEV_OPT_CLOSE_ON_FREE)
+		evutil_closesocket(lev_iocp->fd);
+
 	UNLOCK(lev);
 	return 0;
 }