diff --git a/proxy/tg_ws_proxy.py b/proxy/tg_ws_proxy.py
index 3869749..92c5c12 100644
--- a/proxy/tg_ws_proxy.py
+++ b/proxy/tg_ws_proxy.py
@@ -521,14 +521,19 @@ async def _run(stop_event: Optional[asyncio.Event] = None):
                     return_when=asyncio.FIRST_COMPLETED,
                 )
                 if stop_task in done:
-                    server.close()
-                    await server.wait_closed()
+                    for task in list(_client_tasks):
+                        task.cancel()
+                    if _client_tasks:
+                        await asyncio.gather(
+                            *_client_tasks, return_exceptions=True)
                     if not serve_task.done():
                         serve_task.cancel()
                         try:
                             await serve_task
                         except asyncio.CancelledError:
                             pass
+                    server.close()
+                    await server.wait_closed()
                 else:
                     stop_task.cancel()
                     try:
diff --git a/utils/tray_common.py b/utils/tray_common.py
index 1582833..503dc4e 100644
--- a/utils/tray_common.py
+++ b/utils/tray_common.py
@@ -364,6 +364,9 @@ def stop_proxy() -> None:
         loop.call_soon_threadsafe(stop_ev.set)
         if _proxy_thread:
             _proxy_thread.join(timeout=5)
+            if _proxy_thread.is_alive():
+                log.warning("Proxy thread did not stop within timeout; "
+                            "port may still be in use")
     _proxy_thread = None
     log.info("Proxy stopped")
 
@@ -371,7 +374,7 @@ def stop_proxy() -> None:
 def restart_proxy(cfg: dict, on_error: Callable[[str], None]) -> None:
     log.info("Restarting proxy...")
     stop_proxy()
-    time.sleep(0.3)
+    time.sleep(1.0)
     start_proxy(cfg, on_error)