diff --git a/Intersect.Client.Core/Interface/Game/SimplifiedEscapeMenu.cs b/Intersect.Client.Core/Interface/Game/SimplifiedEscapeMenu.cs
index 0007d7c403..2812fe208c 100644
--- a/Intersect.Client.Core/Interface/Game/SimplifiedEscapeMenu.cs
+++ b/Intersect.Client.Core/Interface/Game/SimplifiedEscapeMenu.cs
@@ -6,8 +6,8 @@
 using Intersect.Client.General;
 using Intersect.Client.Interface.Shared;
 using Intersect.Client.Localization;
+using Intersect.Client.MonoGame;
 using Intersect.Framework.Core;
-using Intersect.Utilities;
 
 namespace Intersect.Client.Interface.Game;
 
@@ -114,6 +114,11 @@ private void LogoutToMainToMainMenuClicked(Base sender, MouseButtonState argumen
 
     private void ExitToDesktopClicked(Base sender, MouseButtonState arguments)
     {
+        if (IntersectGame._isShowingExitConfirmation)
+        {
+            return;
+        }
+
         if (Globals.Me?.CombatTimer > Timing.Global?.Milliseconds)
         {
             AlertWindow.Open(
@@ -123,8 +128,13 @@ private void ExitToDesktopClicked(Base sender, MouseButtonState arguments)
                 inputType: InputType.YesNo,
                 handleSubmit: (_, _) =>
                 {
+                    IntersectGame._isShowingExitConfirmation = false;
                     Globals.Me.CombatTimer = 0;
                     Globals.IsRunning = false;
+                },
+                handleCancel: (_, _) =>
+                {
+                    IntersectGame._isShowingExitConfirmation = false;
                 }
             );
         }
@@ -137,10 +147,17 @@ private void ExitToDesktopClicked(Base sender, MouseButtonState arguments)
                 inputType: InputType.YesNo,
                 handleSubmit: (_, _) =>
                 {
+                    IntersectGame._isShowingExitConfirmation = false;
                     Globals.IsRunning = false;
+                },
+                handleCancel: (_, _) =>
+                {
+                    IntersectGame._isShowingExitConfirmation = false;
                 }
             );
         }
+
+        IntersectGame._isShowingExitConfirmation = true;
     }
 
     private void OpenSettingsWindow(object? sender, EventArgs? e)
diff --git a/Intersect.Client.Core/Interface/Menu/EscapeMenuWindow.cs b/Intersect.Client.Core/Interface/Menu/EscapeMenuWindow.cs
index 22d483c3a6..9c96c46102 100644
--- a/Intersect.Client.Core/Interface/Menu/EscapeMenuWindow.cs
+++ b/Intersect.Client.Core/Interface/Menu/EscapeMenuWindow.cs
@@ -5,8 +5,8 @@
 using Intersect.Client.General;
 using Intersect.Client.Interface.Shared;
 using Intersect.Client.Localization;
+using Intersect.Client.MonoGame;
 using Intersect.Framework.Core;
-using Intersect.Utilities;
 
 namespace Intersect.Client.Interface.Menu;
 
@@ -217,6 +217,11 @@ private void ShowCombatWarning()
 
     private void ExitToDesktop(object? sender, EventArgs? e)
     {
+        if (IntersectGame._isShowingExitConfirmation)
+        {
+            return;
+        }
+
         AlertWindow.Open(
             Strings.General.QuitPrompt,
             Strings.General.QuitTitle,
@@ -229,8 +234,15 @@ private void ExitToDesktop(object? sender, EventArgs? e)
                     Globals.Me.CombatTimer = 0;
                 }
 
+                IntersectGame._isShowingExitConfirmation = false;
                 Globals.IsRunning = false;
+            },
+            handleCancel: (_, _) =>
+            {
+                IntersectGame._isShowingExitConfirmation = false;
             }
         );
+
+        IntersectGame._isShowingExitConfirmation = true;
     }
 }
\ No newline at end of file
diff --git a/Intersect.Client.Core/Interface/Shared/AlertWindow.cs b/Intersect.Client.Core/Interface/Shared/AlertWindow.cs
index 74e91a9d58..6c492019d9 100644
--- a/Intersect.Client.Core/Interface/Shared/AlertWindow.cs
+++ b/Intersect.Client.Core/Interface/Shared/AlertWindow.cs
@@ -20,6 +20,7 @@ public record struct Alert(string Message, string? Title = default, AlertType Ty
 public class AlertWindow : InputBox
 {
     private static readonly HashSet<AlertWindow> _instances = [];
+    private readonly GwenEventHandler<EventArgs>? _handleCancel;
 
     private AlertWindow(
         string title,
@@ -39,6 +40,8 @@ private AlertWindow(
         userData: userData
     )
     {
+        _handleCancel = handleCancel;
+
         Icon = GameContentManager.Current.GetTexture(
             TextureType.Gui,
             $"icon.alert.{alertType.ToString().ToLowerInvariant()}.png"
@@ -49,6 +52,15 @@ private AlertWindow(
 
         var titleLabelMargin = TitleLabel.Margin;
         TitleLabel.Margin = titleLabelMargin with { Left = titleLabelMargin.Left + 4 };
+
+        // Subscribe to the Closed event to handle X button clicks
+        Closed += OnWindowClosed;
+    }
+
+    private void OnWindowClosed(Base sender, EventArgs args)
+    {
+        // Trigger the cancel handler when window is closed via X button
+        _handleCancel?.Invoke(this, args);
     }
 
     protected override void OnCanceled(Base sender, EventArgs args)
diff --git a/Intersect.Client.Core/MonoGame/IntersectGame.cs b/Intersect.Client.Core/MonoGame/IntersectGame.cs
index dbb9e0fb4d..9248855e37 100644
--- a/Intersect.Client.Core/MonoGame/IntersectGame.cs
+++ b/Intersect.Client.Core/MonoGame/IntersectGame.cs
@@ -11,8 +11,6 @@
 using Intersect.Configuration;
 using Microsoft.Xna.Framework;
 using Microsoft.Xna.Framework.Graphics;
-using System.Diagnostics;
-using System.Reflection;
 using Intersect.Client.Framework.Database;
 using Intersect.Client.Framework.Graphics;
 using Intersect.Client.ThirdParty;
@@ -58,6 +56,8 @@ internal partial class IntersectGame : Game
     private SpriteBatch? updateBatch;
 
     private bool updaterGraphicsReset;
+    
+    public static bool _isShowingExitConfirmation;
 
     #endregion
 
@@ -355,6 +355,11 @@ protected override void OnExiting(object sender, ExitingEventArgs args)
                         Globals.Me.CombatTimer > Timing.Global?.Milliseconds &&
                         Globals.GameState == GameStates.InGame;
 
+        if (_isShowingExitConfirmation)
+        {
+            return;
+        }
+
         if (inCombat)
         {
             AlertWindow.Open(
@@ -369,7 +374,12 @@ protected override void OnExiting(object sender, ExitingEventArgs args)
                         Globals.Me.CombatTimer = 0;
                     }
 
+                    _isShowingExitConfirmation = false;
                     Globals.IsRunning = false;
+                },
+                handleCancel: (_, _) =>
+                {
+                    _isShowingExitConfirmation = false;
                 }
             );
         }
@@ -382,10 +392,16 @@ protected override void OnExiting(object sender, ExitingEventArgs args)
                 inputType: InputType.YesNo,
                 handleSubmit: (_, _) =>
                 {
+                    _isShowingExitConfirmation = false;
                     Globals.IsRunning = false;
+                },
+                handleCancel: (_, _) =>
+                {
+                    _isShowingExitConfirmation = false;
                 }
             );
         }
+        _isShowingExitConfirmation = true;
     }
 
     private void TryExit(object sender, ExitingEventArgs args)