diff --git a/src/Files.App/App.xaml.cs b/src/Files.App/App.xaml.cs
index 653422bc2ff47..baef7548d0237 100644
--- a/src/Files.App/App.xaml.cs
+++ b/src/Files.App/App.xaml.cs
@@ -2,7 +2,6 @@
 using CommunityToolkit.WinUI;
 using CommunityToolkit.WinUI.Helpers;
 using CommunityToolkit.WinUI.Notifications;
-using Files.App.Controllers;
 using Files.App.DataModels;
 using Files.App.Extensions;
 using Files.App.Filesystem;
@@ -30,6 +29,7 @@
 using Microsoft.Extensions.DependencyInjection;
 using Microsoft.UI.Windowing;
 using Microsoft.UI.Xaml;
+using Microsoft.UI.Xaml.Controls;
 using Microsoft.Windows.AppLifecycle;
 using System;
 using System.Diagnostics;
@@ -54,6 +54,7 @@ public partial class App : Application
 		private static bool ShowErrorNotification = false;
 
 		public static string OutputPath { get; set; }
+		public static CommandBarFlyout? LastOpenedFlyout { get; set; }
 		public static StorageHistoryWrapper HistoryWrapper = new StorageHistoryWrapper();
 		public static SettingsViewModel AppSettings { get; private set; }
 		public static AppModel AppModel { get; private set; }
@@ -287,6 +288,15 @@ private async void Window_Closed(object sender, WindowEventArgs args)
 		{
 			// Save application state and stop any background activity
 
+			// A Workaround for the crash (#10110)
+			if (LastOpenedFlyout?.IsOpen ?? false)
+			{
+				args.Handled = true;
+				LastOpenedFlyout.Closed += (sender, e) => App.Current.Exit();
+				LastOpenedFlyout.Hide();
+				return;
+			}
+
 			await Task.Yield(); // Method can take a long time, make sure the window is hidden
 
 			SaveSessionTabs();
diff --git a/src/Files.App/BaseLayout.cs b/src/Files.App/BaseLayout.cs
index 21759ce74dbbb..3d6f5deb08e4c 100644
--- a/src/Files.App/BaseLayout.cs
+++ b/src/Files.App/BaseLayout.cs
@@ -563,6 +563,8 @@ public async void ItemContextFlyout_Opening(object? sender, object e)
 
 				if (IsItemSelected)
 					await LoadMenuItemsAsync();
+
+				App.LastOpenedFlyout = sender as CommandBarFlyout;
 			}
 			catch (Exception error)
 			{
@@ -607,6 +609,8 @@ public async void BaseContextFlyout_Opening(object? sender, object e)
 					else
 						RemoveOverflow(BaseContextMenuFlyout);
 				}
+
+				App.LastOpenedFlyout = sender as CommandBarFlyout;
 			}
 			catch (Exception error)
 			{
diff --git a/src/Files.App/UserControls/SidebarControl.xaml.cs b/src/Files.App/UserControls/SidebarControl.xaml.cs
index 90667df4cf35e..3199067348fca 100644
--- a/src/Files.App/UserControls/SidebarControl.xaml.cs
+++ b/src/Files.App/UserControls/SidebarControl.xaml.cs
@@ -420,6 +420,7 @@ private void PaneRoot_RightTapped(object sender, RightTappedRoutedEventArgs e)
 		private void NavigationViewItem_RightTapped(object sender, RightTappedRoutedEventArgs e)
 		{
 			var itemContextMenuFlyout = new CommandBarFlyout { Placement = FlyoutPlacementMode.Full };
+			itemContextMenuFlyout.Opening += (sender, e) => App.LastOpenedFlyout = sender as CommandBarFlyout;
 			if (sender is not NavigationViewItem sidebarItem ||
 				sidebarItem.DataContext is not INavigationControlItem item)
 				return;
diff --git a/src/Files.App/UserControls/Widgets/FileTagsWidget.xaml.cs b/src/Files.App/UserControls/Widgets/FileTagsWidget.xaml.cs
index 30a85ebc2f78a..24bf21f11c756 100644
--- a/src/Files.App/UserControls/Widgets/FileTagsWidget.xaml.cs
+++ b/src/Files.App/UserControls/Widgets/FileTagsWidget.xaml.cs
@@ -65,6 +65,7 @@ private async void FileTagItem_ItemClick(object sender, ItemClickEventArgs e)
 		private void Item_RightTapped(object sender, RightTappedRoutedEventArgs e)
 		{
 			var itemContextMenuFlyout = new CommandBarFlyout { Placement = FlyoutPlacementMode.Full };
+			itemContextMenuFlyout.Opening += (sender, e) => App.LastOpenedFlyout = sender as CommandBarFlyout;
 			if (sender is not StackPanel tagsItemsStackPanel || tagsItemsStackPanel.DataContext is not FileTagsItemViewModel item)
 				return;
 			itemContextMenuFlyout.ShowAt(tagsItemsStackPanel, new FlyoutShowOptions { Position = e.GetPosition(tagsItemsStackPanel) });
diff --git a/src/Files.App/UserControls/Widgets/HomePageWidget.cs b/src/Files.App/UserControls/Widgets/HomePageWidget.cs
index e71c44ae04e52..b7ed0572f4d8f 100644
--- a/src/Files.App/UserControls/Widgets/HomePageWidget.cs
+++ b/src/Files.App/UserControls/Widgets/HomePageWidget.cs
@@ -47,6 +47,7 @@ public abstract class HomePageWidget : UserControl
 		public void Button_RightTapped(object sender, RightTappedRoutedEventArgs e)
 		{
 			var itemContextMenuFlyout = new CommandBarFlyout { Placement = FlyoutPlacementMode.Full };
+			itemContextMenuFlyout.Opening += (sender, e) => App.LastOpenedFlyout = sender as CommandBarFlyout;
 			if (sender is not Button widgetCardItem || widgetCardItem.DataContext is not WidgetCardItem item)
 				return;
 
diff --git a/src/Files.App/UserControls/Widgets/RecentFilesWidget.xaml.cs b/src/Files.App/UserControls/Widgets/RecentFilesWidget.xaml.cs
index 5b1613765d681..fbef8198e88ca 100644
--- a/src/Files.App/UserControls/Widgets/RecentFilesWidget.xaml.cs
+++ b/src/Files.App/UserControls/Widgets/RecentFilesWidget.xaml.cs
@@ -109,6 +109,7 @@ public RecentFilesWidget()
 		private void Grid_RightTapped(object sender, RightTappedRoutedEventArgs e)
 		{
 			var itemContextMenuFlyout = new CommandBarFlyout { Placement = FlyoutPlacementMode.Full };
+			itemContextMenuFlyout.Opening += (sender, e) => App.LastOpenedFlyout = sender as CommandBarFlyout;
 			if (sender is not Grid recentItemsGrid || recentItemsGrid.DataContext is not RecentItem item)
 				return;