diff --git a/Intersect.Client.Core/Interface/Game/SimplifiedEscapeMenu.cs b/Intersect.Client.Core/Interface/Game/SimplifiedEscapeMenu.cs
index a381d5d171..0007d7c403 100644
--- a/Intersect.Client.Core/Interface/Game/SimplifiedEscapeMenu.cs
+++ b/Intersect.Client.Core/Interface/Game/SimplifiedEscapeMenu.cs
@@ -35,7 +35,7 @@ public SimplifiedEscapeMenu(Canvas gameCanvas, Func<SettingsWindow> settingsWind
         _settings.Clicked += OpenSettingsWindow;
         _character.Clicked += LogoutToCharacterSelectSelectClicked;
         _logout.Clicked += LogoutToMainToMainMenuClicked;
-        _exit.Clicked += ExitToDesktopToDesktopClicked;
+        _exit.Clicked += ExitToDesktopClicked;
 
         LoadJsonUi(GameContentManager.UI.InGame, Graphics.Renderer?.GetResolutionString());
     }
@@ -80,7 +80,13 @@ private void LogoutToCharacterSelectSelectClicked(Base sender, MouseButtonState
     {
         if (Globals.Me?.CombatTimer > Timing.Global.Milliseconds)
         {
-            ShowCombatWarning();
+            AlertWindow.Open(
+                Strings.Combat.WarningCharacterSelect,
+                Strings.Combat.WarningTitle,
+                AlertType.Warning,
+                handleSubmit: LogoutToCharacterSelect,
+                inputType: InputType.YesNo
+            );
         }
         else
         {
@@ -92,7 +98,13 @@ private void LogoutToMainToMainMenuClicked(Base sender, MouseButtonState argumen
     {
         if (Globals.Me?.CombatTimer > Timing.Global.Milliseconds)
         {
-            ShowCombatWarning();
+            AlertWindow.Open(
+                Strings.Combat.WarningLogout,
+                Strings.Combat.WarningTitle,
+                AlertType.Warning,
+                handleSubmit: LogoutToMainMenu,
+                inputType: InputType.YesNo
+            );
         }
         else
         {
@@ -100,29 +112,37 @@ private void LogoutToMainToMainMenuClicked(Base sender, MouseButtonState argumen
         }
     }
 
-    private void ExitToDesktopToDesktopClicked(Base sender, MouseButtonState arguments)
+    private void ExitToDesktopClicked(Base sender, MouseButtonState arguments)
     {
-        if (Globals.Me?.CombatTimer > Timing.Global.Milliseconds)
+        if (Globals.Me?.CombatTimer > Timing.Global?.Milliseconds)
         {
-            ShowCombatWarning();
+            AlertWindow.Open(
+                Strings.Combat.WarningExitDesktop,
+                Strings.Combat.WarningTitle,
+                AlertType.Warning,
+                inputType: InputType.YesNo,
+                handleSubmit: (_, _) =>
+                {
+                    Globals.Me.CombatTimer = 0;
+                    Globals.IsRunning = false;
+                }
+            );
         }
         else
         {
-            ExitToDesktop(null, null);
+            AlertWindow.Open(
+                Strings.General.QuitPrompt,
+                Strings.General.QuitTitle,
+                AlertType.Warning,
+                inputType: InputType.YesNo,
+                handleSubmit: (_, _) =>
+                {
+                    Globals.IsRunning = false;
+                }
+            );
         }
     }
 
-    private static void ShowCombatWarning()
-    {
-        AlertWindow.Open(
-            Strings.Combat.WarningCharacterSelect,
-            Strings.Combat.WarningTitle,
-            AlertType.Warning,
-            handleSubmit: LogoutToCharacterSelect,
-            inputType: InputType.YesNo
-        );
-    }
-
     private void OpenSettingsWindow(object? sender, EventArgs? e)
     {
         var settingsWindow = _settingsWindowProvider();
@@ -153,23 +173,4 @@ private static void LogoutToMainMenu(object? sender, EventArgs? e)
 
         Main.Logout(false);
     }
-
-    private static void ExitToDesktop(object? sender, EventArgs? e)
-    {
-        AlertWindow.Open(
-            Strings.General.QuitPrompt,
-            Strings.General.QuitTitle,
-            AlertType.Warning,
-            inputType: InputType.YesNo,
-            handleSubmit: (_, _) =>
-            {
-                if (Globals.Me != null)
-                {
-                    Globals.Me.CombatTimer = 0;
-                }
-
-                Globals.IsRunning = false;
-            }
-        );
-    }
 }
\ No newline at end of file
diff --git a/Intersect.Client.Core/MonoGame/IntersectGame.cs b/Intersect.Client.Core/MonoGame/IntersectGame.cs
index b79e245dc9..dbb9e0fb4d 100644
--- a/Intersect.Client.Core/MonoGame/IntersectGame.cs
+++ b/Intersect.Client.Core/MonoGame/IntersectGame.cs
@@ -43,8 +43,6 @@ internal partial class IntersectGame : Game
 
     private GraphicsDeviceManager mGraphics;
 
-    private bool _isShowingExitConfirmation = false;
-
     #region "Autoupdate Variables"
 
     private Updater? _updater;
@@ -341,64 +339,57 @@ protected override void Draw(GameTime gameTime)
 
     protected override void OnExiting(object sender, ExitingEventArgs args)
     {
-        // If already showing dialog, just cancel and return
-        if (_isShowingExitConfirmation)
+        // If game is already shutting down, allow it to exit normally
+        if (!Globals.IsRunning)
         {
-            args.Cancel = true;
+            ApplicationContext.Context.Value?.Logger.LogInformation("System window closing (due to user interaction most likely).");
+            TryExit(sender, args);
             return;
         }
 
-        ApplicationContext.Context.Value?.Logger.LogInformation("System window closing (due to user interaction most likely).");
-
-        // Check if player is logged in and in game
-        if (Globals.Me != null && Globals.LoggedIn && Globals.GameState == GameStates.InGame)
-        {
-            // Set flag to prevent multiple dialogs
-            _isShowingExitConfirmation = true;
-
-            // Check if player is in combat
-            bool inCombat = Globals.Me.CombatTimer > Timing.Global?.Milliseconds;
+        // Cancel the exit event
+        args.Cancel = true;
 
-            // Cancel the exit event
-            args.Cancel = true;
+        // Check if there's a player in combat
+        bool inCombat = Globals.Me != null &&
+                        Globals.Me.CombatTimer > Timing.Global?.Milliseconds &&
+                        Globals.GameState == GameStates.InGame;
 
-            if (inCombat)
-            {
-                // Show combat warning
-                var inputBox = new InputBox(
-                    title: Strings.Combat.WarningTitle,
-                    prompt: Strings.Combat.WarningExitDesktop,
-                    inputType: InputType.YesNo,
-                    onSubmit: (s, e) =>
+        if (inCombat)
+        {
+            AlertWindow.Open(
+                Strings.Combat.WarningExitDesktop,
+                Strings.Combat.WarningTitle,
+                AlertType.Warning,
+                inputType: InputType.YesNo,
+                handleSubmit: (_, _) =>
+                {
+                    if (Globals.Me != null)
                     {
                         Globals.Me.CombatTimer = 0;
-                        _isShowingExitConfirmation = false;
-                        Globals.IsRunning = false;
-                    },
-                    onCancel: (s, e) => { _isShowingExitConfirmation = false; }
-                );
-                inputBox.Closed += (s, e) => { _isShowingExitConfirmation = false; };
-            }
-            else
-            {
-                // Show quit confirmation
-                var inputBox = new InputBox(
-                    title: Strings.General.QuitTitle,
-                    prompt: Strings.General.QuitPrompt,
-                    inputType: InputType.YesNo,
-                    onSubmit: (s, e) =>
-                    {
-                        _isShowingExitConfirmation = false;
-                        Globals.IsRunning = false;
-                    },
-                    onCancel: (s, e) => { _isShowingExitConfirmation = false; }
-                );
-                inputBox.Closed += (s, e) => { _isShowingExitConfirmation = false; };
-            }
+                    }
 
-            return;
+                    Globals.IsRunning = false;
+                }
+            );
         }
+        else
+        {
+            AlertWindow.Open(
+                Strings.General.QuitPrompt,
+                Strings.General.QuitTitle,
+                AlertType.Warning,
+                inputType: InputType.YesNo,
+                handleSubmit: (_, _) =>
+                {
+                    Globals.IsRunning = false;
+                }
+            );
+        }
+    }
 
+    private void TryExit(object sender, ExitingEventArgs args)
+    {
         try
         {
             _updater?.Stop();
diff --git a/Intersect.Client.Framework/Gwen/Control/Base.cs b/Intersect.Client.Framework/Gwen/Control/Base.cs
index b49cb19e8a..eda1d4a7e0 100644
--- a/Intersect.Client.Framework/Gwen/Control/Base.cs
+++ b/Intersect.Client.Framework/Gwen/Control/Base.cs
@@ -861,6 +861,12 @@ public bool IsHidden
 
     private static void SetVisible(Base @this, bool value)
     {
+        // Check if already disposed
+        if (@this._disposed)
+        {
+            return;
+        }
+
         var wasVisibleInParent = @this._visible;
 
         if (@this.GetType().Name == "VersionPanel")
diff --git a/Intersect.Client.Framework/Gwen/Control/WindowControl.cs b/Intersect.Client.Framework/Gwen/Control/WindowControl.cs
index 4f5e8ed22d..cd0765761c 100644
--- a/Intersect.Client.Framework/Gwen/Control/WindowControl.cs
+++ b/Intersect.Client.Framework/Gwen/Control/WindowControl.cs
@@ -273,7 +273,14 @@ private void Close(Base sender, EventArgs args)
             return;
         }
 
-        IsHidden = true;
+        try
+        {
+            IsHidden = true;
+        }
+        catch (ObjectDisposedException)
+        {
+            // Canvas already disposed during shutdown, this is fine
+        }
 
         if (_modal != null)
         {