diff --git a/src/Controls/samples/Controls.Sample/Pages/Core/MultiWindowPage.xaml b/src/Controls/samples/Controls.Sample/Pages/Core/MultiWindowPage.xaml
index 26a69ac68560..4ba2119b2fcd 100644
--- a/src/Controls/samples/Controls.Sample/Pages/Core/MultiWindowPage.xaml
+++ b/src/Controls/samples/Controls.Sample/Pages/Core/MultiWindowPage.xaml
@@ -10,6 +10,11 @@
             Padding="12"
             Spacing="6">
 
+            <WebView
+                HeightRequest="300"
+                WidthRequest="300"
+                Source="https://github.com/dotnet/maui" />
+            
             <Label Text="Current Window Frame:" />
             <Label Text="{Binding Window.X, StringFormat='X = {0:0.00}'}" />
             <Label Text="{Binding Window.Y, StringFormat='Y = {0:0.00}'}" />
diff --git a/src/Core/src/Handlers/WebView/WebViewHandler.Windows.cs b/src/Core/src/Handlers/WebView/WebViewHandler.Windows.cs
index 878bb1a90283..d985a7e3dea9 100644
--- a/src/Core/src/Handlers/WebView/WebViewHandler.Windows.cs
+++ b/src/Core/src/Handlers/WebView/WebViewHandler.Windows.cs
@@ -2,6 +2,7 @@
 using System.Collections.Generic;
 using System.Linq;
 using System.Net;
+using Microsoft.UI.Xaml;
 using Microsoft.UI.Xaml.Controls;
 using Microsoft.Web.WebView2.Core;
 using Windows.Web.Http;
@@ -12,6 +13,7 @@ public partial class WebViewHandler : ViewHandler<IWebView, WebView2>
 	{
 		WebNavigationEvent _eventState;
 		readonly HashSet<string> _loadedCookies = new HashSet<string>();
+		Window? _window;
 
 		protected override WebView2 CreatePlatformView() => new MauiWebView();
 
@@ -24,21 +26,54 @@ internal WebNavigationEvent CurrentNavigationEvent
 		protected override void ConnectHandler(WebView2 platformView)
 		{
 			platformView.CoreWebView2Initialized += OnCoreWebView2Initialized;
-
 			base.ConnectHandler(platformView);
+
+			if (platformView.IsLoaded)
+				OnLoaded();
+			else
+				platformView.Loaded += OnWebViewLoaded;
 		}
 
-		protected override void DisconnectHandler(WebView2 platformView)
+		void OnWebViewLoaded(object sender, UI.Xaml.RoutedEventArgs e)
+		{
+			OnLoaded();
+		}
+
+		void OnLoaded()
+		{
+			_window = MauiContext!.GetPlatformWindow();
+			_window.Closed += OnWindowClosed;
+		}
+
+		private void OnWindowClosed(object sender, UI.Xaml.WindowEventArgs args)
 		{
-			if (platformView.CoreWebView2 != null)
+			Disconnect(PlatformView);
+		}
+
+		void Disconnect(WebView2 platformView)
+		{
+			if (_window is not null)
+			{
+				_window.Closed -= OnWindowClosed;
+				_window = null;
+			}
+
+			if (platformView.CoreWebView2 is not null)
 			{
 				platformView.CoreWebView2.HistoryChanged -= OnHistoryChanged;
 				platformView.CoreWebView2.NavigationStarting -= OnNavigationStarting;
 				platformView.CoreWebView2.NavigationCompleted -= OnNavigationCompleted;
+				platformView.CoreWebView2.Stop();
 			}
 
+			platformView.Loaded -= OnWebViewLoaded;
 			platformView.CoreWebView2Initialized -= OnCoreWebView2Initialized;
+			platformView.Close();
+		}
 
+		protected override void DisconnectHandler(WebView2 platformView)
+		{
+			DisconnectHandler(platformView);
 			base.DisconnectHandler(platformView);
 		}
 
@@ -66,7 +101,7 @@ void OnNavigationCompleted(CoreWebView2 sender, CoreWebView2NavigationCompletedE
 
 		void OnNavigationStarting(CoreWebView2 sender, CoreWebView2NavigationStartingEventArgs args)
 		{
-			if (Uri.TryCreate(args.Uri, UriKind.Absolute, out Uri? uri) && uri != null)
+			if (Uri.TryCreate(args.Uri, UriKind.Absolute, out Uri? uri) && uri is not null)
 			{
 				bool cancel = VirtualView.Navigating(CurrentNavigationEvent, uri.AbsoluteUri);
 
@@ -126,7 +161,7 @@ void NavigationSucceeded(CoreWebView2 sender, CoreWebView2NavigationCompletedEve
 		{
 			var uri = sender.Source;
 
-			if (uri != null)
+			if (uri is not null)
 				SendNavigated(uri, CurrentNavigationEvent, WebNavigationResult.Success);
 
 			if (VirtualView is null)
@@ -145,12 +180,11 @@ void NavigationFailed(CoreWebView2 sender, CoreWebView2NavigationCompletedEventA
 
 		void SendNavigated(string url, WebNavigationEvent evnt, WebNavigationResult result)
 		{
-			if (VirtualView != null)
+			if (VirtualView is not null)
 			{
 				SyncPlatformCookiesToVirtualView(url);
 
 				VirtualView.Navigated(evnt, url, result);
-
 				PlatformView?.UpdateCanGoBackForward(VirtualView);
 			}
 
@@ -161,12 +195,12 @@ void SyncPlatformCookiesToVirtualView(string url)
 		{
 			var myCookieJar = VirtualView.Cookies;
 
-			if (myCookieJar == null)
+			if (myCookieJar is null)
 				return;
 
 			var uri = CreateUriForCookies(url);
 
-			if (uri == null)
+			if (uri is null)
 				return;
 
 			var cookies = myCookieJar.GetCookies(uri);
@@ -180,7 +214,7 @@ void SyncPlatformCookiesToVirtualView(string url)
 				var httpCookie = platformCookies
 					.FirstOrDefault(x => x.Name == cookie.Name);
 
-				if (httpCookie == null)
+				if (httpCookie is null)
 					cookie.Expired = true;
 				else
 					cookie.Value = httpCookie.Value;
@@ -193,18 +227,18 @@ void SyncPlatformCookies(string url)
 		{
 			var uri = CreateUriForCookies(url);
 
-			if (uri == null)
+			if (uri is null)
 				return;
 
 			var myCookieJar = VirtualView.Cookies;
 
-			if (myCookieJar == null)
+			if (myCookieJar is null)
 				return;
 
 			InitialCookiePreloadIfNecessary(url);
 			var cookies = myCookieJar.GetCookies(uri);
 
-			if (cookies == null)
+			if (cookies is null)
 				return;
 
 			var retrieveCurrentWebCookies = GetCookiesFromPlatformStore(url);
@@ -222,7 +256,7 @@ void SyncPlatformCookies(string url)
 
 			foreach (HttpCookie cookie in retrieveCurrentWebCookies)
 			{
-				if (cookies[cookie.Name] != null)
+				if (cookies[cookie.Name] is not null)
 					continue;
 
 				filter.CookieManager.DeleteCookie(cookie);
@@ -233,7 +267,7 @@ void InitialCookiePreloadIfNecessary(string url)
 		{
 			var myCookieJar = VirtualView.Cookies;
 
-			if (myCookieJar == null)
+			if (myCookieJar is null)
 				return;
 
 			var uri = new Uri(url);
@@ -243,12 +277,12 @@ void InitialCookiePreloadIfNecessary(string url)
 
 			var cookies = myCookieJar.GetCookies(uri);
 
-			if (cookies != null)
+			if (cookies is not null)
 			{
 				var existingCookies = GetCookiesFromPlatformStore(url);
 				foreach (HttpCookie cookie in existingCookies)
 				{
-					if (cookies[cookie.Name] == null)
+					if (cookies[cookie.Name] is null)
 						myCookieJar.SetCookies(uri, cookie.ToString());
 				}
 			}
@@ -265,7 +299,7 @@ HttpCookieCollection GetCookiesFromPlatformStore(string url)
 
 		Uri? CreateUriForCookies(string url)
 		{
-			if (url == null)
+			if (url is null)
 				return null;
 
 			Uri? uri;
@@ -290,7 +324,7 @@ public static void MapEvaluateJavaScriptAsync(IWebViewHandler handler, IWebView
 		{
 			if (arg is EvaluateJavaScriptAsyncRequest request)
 			{
-				if (handler.PlatformView == null)
+				if (handler.PlatformView is null)
 				{
 					request.SetCanceled();
 					return;
diff --git a/src/Core/tests/DeviceTests.Shared/Stubs/ContextStub.cs b/src/Core/tests/DeviceTests.Shared/Stubs/ContextStub.cs
index b81f8c2d8bdb..42b5e0c460a6 100644
--- a/src/Core/tests/DeviceTests.Shared/Stubs/ContextStub.cs
+++ b/src/Core/tests/DeviceTests.Shared/Stubs/ContextStub.cs
@@ -46,7 +46,7 @@ public object GetService(Type serviceType)
 				return _windowManager ??= new NavigationRootManager(MauiProgramDefaults.DefaultWindow);
 
 			if (serviceType == typeof(UI.Xaml.Window))
-				return MauiProgramDefaults.DefaultWindow;
+				return _services.GetService(serviceType) ?? MauiProgramDefaults.DefaultWindow;
 #endif
 			if (serviceType == typeof(IDispatcher))
 				return _services.GetService(serviceType) ?? TestDispatcher.Current;
diff --git a/src/Core/tests/DeviceTests/Handlers/WebView/WebViewHandlerTests.Windows.cs b/src/Core/tests/DeviceTests/Handlers/WebView/WebViewHandlerTests.Windows.cs
index efedc99bf5ce..909237121303 100644
--- a/src/Core/tests/DeviceTests/Handlers/WebView/WebViewHandlerTests.Windows.cs
+++ b/src/Core/tests/DeviceTests/Handlers/WebView/WebViewHandlerTests.Windows.cs
@@ -1,9 +1,46 @@
-using Microsoft.UI.Xaml.Controls;
+using System.Threading.Tasks;
+using Microsoft.Extensions.DependencyInjection;
+using Microsoft.Maui.Controls;
+using Microsoft.Maui.DeviceTests.Stubs;
+using Microsoft.UI.Xaml.Controls;
+using Xunit;
 
 namespace Microsoft.Maui.DeviceTests
 {
 	public partial class WebViewHandlerTests
 	{
+		[Fact(DisplayName = "Closing Window With WebView Doesnt Crash")]
+		public async Task ClosingWindowWithWebViewDoesntCrash()
+		{
+			EnsureHandlerCreated(builder =>
+			{
+				builder.Services.AddSingleton(typeof(UI.Xaml.Window), (services) => new UI.Xaml.Window());
+			});
+
+			var webView = new WebViewStub()
+			{
+				Source = new UrlWebViewSourceStub { Url = "https://dotnet.microsoft.com/" }
+			};
+
+			var handler = await CreateHandlerAsync(webView);
+
+			await InvokeOnMainThreadAsync(async () =>
+			{
+				TaskCompletionSource navigationComplete = new TaskCompletionSource();
+				handler.PlatformView.NavigationCompleted += (_, _) =>
+				{
+					navigationComplete?.SetResult();
+					navigationComplete = null;
+				};
+
+				await handler.PlatformView.AttachAndRun(async () =>
+				{
+					await handler.PlatformView.OnLoadedAsync();
+					await navigationComplete.Task;
+				}, MauiContext);
+			});
+		}
+
 		WebView2 GetNativeWebView(WebViewHandler webViewHandler) =>
 			webViewHandler.PlatformView;
 
diff --git a/src/TestUtils/src/DeviceTests/AssertionExtensions.Windows.cs b/src/TestUtils/src/DeviceTests/AssertionExtensions.Windows.cs
index 5c32f8944364..4bf62d305647 100644
--- a/src/TestUtils/src/DeviceTests/AssertionExtensions.Windows.cs
+++ b/src/TestUtils/src/DeviceTests/AssertionExtensions.Windows.cs
@@ -93,25 +93,25 @@ public static WColor ColorAtPoint(this CanvasBitmap bitmap, int x, int y, bool i
 				: WColor.FromArgb(255, pixel.R, pixel.G, pixel.B);
 		}
 
-		public static Task AttachAndRun(this FrameworkElement view, Action action) =>
-			view.AttachAndRun(window => action());
+		public static Task AttachAndRun(this FrameworkElement view, Action action, IMauiContext? mauiContext = null) =>
+			view.AttachAndRun(window => action(), mauiContext);
 
-		public static Task AttachAndRun(this FrameworkElement view, Action<Window> action) =>
+		public static Task AttachAndRun(this FrameworkElement view, Action<Window> action, IMauiContext? mauiContext = null) =>
 			view.AttachAndRun((window) =>
 			{
 				action(window);
 				return Task.FromResult(true);
-			});
+			}, mauiContext);
 
-		public static Task<T> AttachAndRun<T>(this FrameworkElement view, Func<T> action) =>
-			view.AttachAndRun(window => action());
+		public static Task<T> AttachAndRun<T>(this FrameworkElement view, Func<T> action, IMauiContext? mauiContext = null) =>
+			view.AttachAndRun(window => action(), mauiContext);
 
-		public static Task<T> AttachAndRun<T>(this FrameworkElement view, Func<Window, T> action) =>
+		public static Task<T> AttachAndRun<T>(this FrameworkElement view, Func<Window, T> action, IMauiContext? mauiContext = null) =>
 			view.AttachAndRun((window) =>
 			{
 				var result = action(window);
 				return Task.FromResult(result);
-			});
+			}, mauiContext);
 
 		public static Task AttachAndRun(this FrameworkElement view, Func<Task> action) =>
 			view.AttachAndRun(window => action());
@@ -132,7 +132,7 @@ public static Task AttachAndRun(this FrameworkElement view, Func<Window, Task> a
 		public static Task<T> AttachAndRun<T>(this FrameworkElement view, Func<Task<T>> action) =>
 			view.AttachAndRun(window => action());
 
-		public static async Task<T> AttachAndRun<T>(this FrameworkElement view, Func<Window, Task<T>> action)
+		public static async Task<T> AttachAndRun<T>(this FrameworkElement view, Func<Window, Task<T>> action, IMauiContext? mauiContext = null)
 		{
 			if (view.Parent is Border wrapper)
 				view = wrapper;
@@ -156,26 +156,27 @@ public static async Task<T> AttachAndRun<T>(this FrameworkElement view, Func<Win
 
 					// attach to the UI
 					Grid grid;
-					var window = new Window
+					var window = (mauiContext?.Services != null) ?
+						Extensions.DependencyInjection.ActivatorUtilities.GetServiceOrCreateInstance<Window>(mauiContext.Services) : new Window();
+
+					window.Content = new Grid
 					{
-						Content = new Grid
+						HorizontalAlignment = HorizontalAlignment.Center,
+						VerticalAlignment = VerticalAlignment.Center,
+						Children =
 						{
-							HorizontalAlignment = HorizontalAlignment.Center,
-							VerticalAlignment = VerticalAlignment.Center,
-							Children =
+							(grid = new Grid
 							{
-								(grid = new Grid
+								Width = view.Width,
+								Height = view.Height,
+								Children =
 								{
-									Width = view.Width,
-									Height = view.Height,
-									Children =
-									{
-										view
-									}
-								})
-							}
+									view
+								}
+							})
 						}
 					};
+
 					window.Activate();
 
 					// wait for element to be loaded