diff --git a/app/app.py b/app/app.py
index bc7eb6f..a34546d 100644
--- a/app/app.py
+++ b/app/app.py
@@ -73,7 +73,6 @@ class ICRAApp(
         self.bring_to_front()
 
     def _setup_window(self) -> None:
-        self.root.overrideredirect(True)
         screen_width = self.root.winfo_screenwidth()
         screen_height = self.root.winfo_screenheight()
         default_width = int(screen_width * 0.8)
@@ -84,15 +83,7 @@ class ICRAApp(
         self._is_maximized = True
         self.root.geometry(f"{screen_width}x{screen_height}+0+0")
         self.root.configure(bg="#f2f2f7")
-        self.root.bind("<Map>", self._restore_borderless)
-        self.root.after(0, self._ensure_taskbar_entry)
-
-    def _restore_borderless(self, _event=None) -> None:
-        try:
-            self.root.overrideredirect(True)
-            self._ensure_taskbar_entry()
-        except Exception:
-            pass
+        self._init_window_chrome()
 
     def _ensure_taskbar_entry(self) -> None:
         """Force the borderless window to show up in the Windows taskbar."""
@@ -105,6 +96,7 @@ class ICRAApp(
             import ctypes
             hwnd = self.root.winfo_id()
             if not hwnd:
+                self.root.after(50, self._ensure_taskbar_entry)
                 return
 
             GWL_EXSTYLE = -20
@@ -137,6 +129,63 @@ class ICRAApp(
         except Exception:
             pass
 
+    def _init_window_chrome(self) -> None:
+        """Configure a borderless window while retaining a taskbar entry."""
+        try:
+            import platform
+
+            system = platform.system()
+            if system == "Windows":
+                self.root.after(0, self._apply_windows_borderless_style)
+                self.root.after(0, self._ensure_taskbar_entry)
+            else:
+                self.root.overrideredirect(True)
+        except Exception:
+            self.root.overrideredirect(True)
+
+    def _apply_windows_borderless_style(self) -> None:
+        try:
+            import platform
+            import ctypes
+
+            if platform.system() != "Windows":
+                return
+
+            hwnd = self.root.winfo_id()
+            if not hwnd:
+                self.root.after(50, self._apply_windows_borderless_style)
+                return
+
+            user32 = ctypes.windll.user32  # type: ignore[attr-defined]
+            GWL_STYLE = -16
+            WS_CAPTION = 0x00C00000
+            WS_THICKFRAME = 0x00040000
+            WS_MAXIMIZEBOX = 0x00010000
+            WS_MINIMIZEBOX = 0x00020000
+            WS_SYSMENU = 0x00080000
+            SWP_NOSIZE = 0x0001
+            SWP_NOMOVE = 0x0002
+            SWP_NOZORDER = 0x0004
+            SWP_FRAMECHANGED = 0x0020
+
+            style = user32.GetWindowLongW(hwnd, GWL_STYLE)
+            new_style = style & ~(
+                WS_CAPTION | WS_THICKFRAME | WS_MINIMIZEBOX | WS_MAXIMIZEBOX | WS_SYSMENU
+            )
+            if new_style != style:
+                user32.SetWindowLongW(hwnd, GWL_STYLE, new_style)
+                user32.SetWindowPos(
+                    hwnd,
+                    0,
+                    0,
+                    0,
+                    0,
+                    0,
+                    SWP_NOMOVE | SWP_NOSIZE | SWP_NOZORDER | SWP_FRAMECHANGED,
+                )
+        except Exception:
+            pass
+
 
 def start_app() -> None:
     """Entry point used by the CLI script."""