diff --git a/src/Files.App/Helpers/ShellContextMenuHelper.cs b/src/Files.App/Helpers/ShellContextMenuHelper.cs
index 1ec0a4726593..201d73cf4af3 100644
--- a/src/Files.App/Helpers/ShellContextMenuHelper.cs
+++ b/src/Files.App/Helpers/ShellContextMenuHelper.cs
@@ -255,7 +255,15 @@ public static async Task LoadShellMenuItems(string path, CommandBarFlyout itemCo
 					var openWithItem = shellMenuItems.Where(x => (x.Tag as Win32ContextMenuItem)?.CommandString == "openas").ToList().FirstOrDefault();
 					if (openWithItem is not null)
 					{
+						openWithItem.ColoredIcon = new ColoredIconModel()
+						{
+							BaseLayerGlyph = "\uF049",
+							OverlayLayerGlyph = "\uF04A",
+						};
 						var (_, openWithItems) = ItemModelListToContextFlyoutHelper.GetAppBarItemsFromModel(new List<ContextMenuFlyoutItemViewModel>() { openWithItem });
+						var placeholder = itemContextMenuFlyout.SecondaryCommands.Where(x => Equals((x as AppBarButton)?.Tag, "OpenWithPlaceholder")).FirstOrDefault() as AppBarButton;
+						if (placeholder is not null)
+							placeholder.Visibility = Visibility.Collapsed;
 						itemContextMenuFlyout.SecondaryCommands.Insert(0, openWithItems.FirstOrDefault());
 						shellMenuItems.Remove(openWithItem);
 					}
diff --git a/src/Files.App/UserControls/Widgets/RecentFilesWidget.xaml.cs b/src/Files.App/UserControls/Widgets/RecentFilesWidget.xaml.cs
index 4da721f4d626..55c45a4bf655 100644
--- a/src/Files.App/UserControls/Widgets/RecentFilesWidget.xaml.cs
+++ b/src/Files.App/UserControls/Widgets/RecentFilesWidget.xaml.cs
@@ -117,7 +117,7 @@ private void Grid_RightTapped(object sender, RightTappedRoutedEventArgs e)
 			secondaryElements.ForEach(i => itemContextMenuFlyout.SecondaryCommands.Add(i));
 			itemContextMenuFlyout.ShowAt(recentItemsGrid, new FlyoutShowOptions { Position = e.GetPosition(recentItemsGrid) });
 
-			_ = ShellContextmenuHelper.LoadShellMenuItems(item.Path, itemContextMenuFlyout);
+			_ = ShellContextmenuHelper.LoadShellMenuItems(item.Path, itemContextMenuFlyout, showOpenWithMenu: true);
 
 			e.Handled = true;
 		}
@@ -126,6 +126,13 @@ public override List<ContextMenuFlyoutItemViewModel> GetItemMenuItems(WidgetCard
 		{
 			return new List<ContextMenuFlyoutItemViewModel>()
 			{
+				new ContextMenuFlyoutItemViewModel()
+				{
+					Text = "OpenItemsWithCaptionText".GetLocalizedResource(),
+					Glyph = "\uE17D",
+					Tag = "OpenWithPlaceholder",
+					IsEnabled = false
+				},
 				new ContextMenuFlyoutItemViewModel()
 				{
 					Text = "RecentItemRemove/Text".GetLocalizedResource(),