diff --git a/server/src/wled_controller/tray.py b/server/src/wled_controller/tray.py
index 257e804..a60adb5 100644
--- a/server/src/wled_controller/tray.py
+++ b/server/src/wled_controller/tray.py
@@ -4,9 +4,32 @@ import os
 import sys
 import webbrowser
 from pathlib import Path
-from tkinter import messagebox
 from typing import Callable
 
+
+def _confirm(message: str, title: str = "LED Grab") -> bool:
+    """Show a Yes/No confirmation dialog using the Win32 API.
+
+    Uses ``ctypes`` instead of ``tkinter.messagebox`` because the packaged
+    embedded Python distribution does not include the tcl/tk runtime, which
+    causes ``tkinter`` to fail with ``Can't find a usable init.tcl``.
+    """
+    if sys.platform != "win32":
+        # Non-Windows: no tray in practice, but fall back to auto-confirm.
+        return True
+    try:
+        import ctypes
+
+        # MB_YESNO = 0x04, MB_ICONQUESTION = 0x20, MB_SETFOREGROUND = 0x10000
+        # IDYES = 6
+        flags = 0x04 | 0x20 | 0x10000
+        result = ctypes.windll.user32.MessageBoxW(0, message, title, flags)
+        return result == 6
+    except Exception:
+        # If the dialog cannot be shown for any reason, proceed with the action.
+        return True
+
+
 try:
     import pystray
     from PIL import Image
@@ -60,9 +83,10 @@ class TrayManager:
         webbrowser.open(f"http://localhost:{self._port}")
 
     def _restart(self, icon: "pystray.Icon", item: "pystray.MenuItem") -> None:
-        if not messagebox.askyesno("LED Grab", "Restart the server?"):
+        if not _confirm("Restart the server?"):
             return
         from wled_controller.server_ref import _broadcast_restarting
+
         _broadcast_restarting()
         self._icon.stop()
         self._on_exit()
@@ -70,7 +94,7 @@ class TrayManager:
         os.execv(sys.executable, [sys.executable, "-m", "wled_controller"])
 
     def _shutdown(self, icon: "pystray.Icon", item: "pystray.MenuItem") -> None:
-        if not messagebox.askyesno("LED Grab", "Shut down the server?"):
+        if not _confirm("Shut down the server?"):
             return
         self._on_exit()
         self._icon.stop()