diff --git a/.gitignore b/.gitignore
index 880743f..df2410f 100644
--- a/.gitignore
+++ b/.gitignore
@@ -28,3 +28,7 @@ queue_state.json
 system_prompt.yaml
 discord_glhf/__pycache__/bot.cpython-313.pyc
 discord_glhf/handlers/__pycache__/event_handler.cpython-313.pyc
+discord_glhf/__pycache__/api.cpython-313.pyc
+discord_glhf/__pycache__/bot.cpython-313.pyc
+discord_glhf/handlers/__pycache__/event_handler.cpython-313.pyc
+discord_glhf/web/__pycache__/app.cpython-313.pyc
diff --git a/discord_glhf/__pycache__/api.cpython-313.pyc b/discord_glhf/__pycache__/api.cpython-313.pyc
index 9a389a5..85387f5 100644
Binary files a/discord_glhf/__pycache__/api.cpython-313.pyc and b/discord_glhf/__pycache__/api.cpython-313.pyc differ
diff --git a/discord_glhf/__pycache__/bot.cpython-313.pyc b/discord_glhf/__pycache__/bot.cpython-313.pyc
index da38c59..839b875 100644
Binary files a/discord_glhf/__pycache__/bot.cpython-313.pyc and b/discord_glhf/__pycache__/bot.cpython-313.pyc differ
diff --git a/discord_glhf/bot.py b/discord_glhf/bot.py
index 938a191..2d3f7a6 100644
--- a/discord_glhf/bot.py
+++ b/discord_glhf/bot.py
@@ -47,7 +47,7 @@ class DiscordBot:
         self.tool_handler = None
         self.event_handler = None
         self.training_manager = TrainingManager()  # Initialize training manager
-        self.http_server = None
+        self.web_shutdown = None
 
     async def _initialize_services(self) -> None:
         """Initialize API and queue services."""
@@ -84,7 +84,8 @@ class DiscordBot:
                         logger.info("Initializing web interface...")
                         app = init_app(self.event_handler)
                         web_port = 5000
-                        asyncio.create_task(run_webserver(start_port=web_port))
+                        self.web_shutdown = asyncio.Event()
+                        asyncio.create_task(run_webserver(start_port=web_port, shutdown_event=self.web_shutdown))
                         logger.info("Web interface initialized (first available port in range 5000-5009 will be used)")
 
                         # Start API manager
@@ -255,8 +256,12 @@ class DiscordBot:
                 stop_tasks = []
                 if self.training_manager and self.training_manager.is_running:
                     stop_tasks.append(self.training_manager.stop())
-                # Web app will be stopped when the event loop closes
-                logger.info("Web app will be stopped with event loop")
+                # Stop web server gracefully
+                if self.web_shutdown:
+                    logger.info("Stopping web server...")
+                    self.web_shutdown.set()
+                    await asyncio.sleep(1)  # Give web server a moment to shut down
+                    logger.info("Web server stopped")
                 if self.db_pool:
                     stop_tasks.append(self.db_pool.close())
 
diff --git a/discord_glhf/handlers/__pycache__/event_handler.cpython-313.pyc b/discord_glhf/handlers/__pycache__/event_handler.cpython-313.pyc
index 7cab6e0..f0bb42f 100644
Binary files a/discord_glhf/handlers/__pycache__/event_handler.cpython-313.pyc and b/discord_glhf/handlers/__pycache__/event_handler.cpython-313.pyc differ
diff --git a/discord_glhf/web/__pycache__/app.cpython-313.pyc b/discord_glhf/web/__pycache__/app.cpython-313.pyc
index 7f08b3f..e08027e 100644
Binary files a/discord_glhf/web/__pycache__/app.cpython-313.pyc and b/discord_glhf/web/__pycache__/app.cpython-313.pyc differ
diff --git a/discord_glhf/web/app.py b/discord_glhf/web/app.py
index e26c833..3b32a82 100644
--- a/discord_glhf/web/app.py
+++ b/discord_glhf/web/app.py
@@ -67,7 +67,7 @@ async def send_prompt():
     except Exception as e:
         return jsonify({'error': str(e)}), 500
 
-async def run_webserver(start_port=5000):
+async def run_webserver(start_port=5000, shutdown_event=None):
     """Run the web server."""
     import hypercorn.asyncio
     from hypercorn.config import Config
@@ -87,11 +87,14 @@ async def run_webserver(start_port=5000):
 
             logger.info(f"Starting web interface at http://localhost:{port}")
             try:
-                await hypercorn.asyncio.serve(app, config)
-                break
-            except KeyboardInterrupt:
-                logger.info("Web server shutdown requested")
+                await hypercorn.asyncio.serve(app, config,
+                                            shutdown_trigger=shutdown_event.wait if shutdown_event else None)
                 break
+            except Exception as e:
+                if isinstance(e, KeyboardInterrupt) or (shutdown_event and shutdown_event.is_set()):
+                    logger.info("Web server shutdown requested")
+                    break
+                raise
         except OSError:
             if port == start_port + 9:  # Last attempt
                 logger.error(f"Could not find an available port in range {start_port}-{port}")