diff --git a/Files.Launcher/MessageHandlers/ContextMenuHandler.cs b/Files.Launcher/MessageHandlers/ContextMenuHandler.cs
index 7c9d97cad3ac..60b03bdeb7b9 100644
--- a/Files.Launcher/MessageHandlers/ContextMenuHandler.cs
+++ b/Files.Launcher/MessageHandlers/ContextMenuHandler.cs
@@ -124,7 +124,7 @@ private Func<string, bool> FilterMenuItems(bool showOpenMenu)
         {
             var knownItems = new List<string>()
             {
-                "opennew", "openas", "opencontaining", "opennewprocess",
+                "opennew", "opencontaining", "opennewprocess",
                 "runas", "runasuser", "pintohome", "PinToStartScreen",
                 "cut", "copy", "paste", "delete", "properties", "link",
                 "Windows.ModernShare", "Windows.Share", "setdesktopwallpaper",
diff --git a/Files/BaseLayout.cs b/Files/BaseLayout.cs
index a38b9216b28b..8269eac09daa 100644
--- a/Files/BaseLayout.cs
+++ b/Files/BaseLayout.cs
@@ -612,6 +612,7 @@ private async Task LoadMenuItemsAsync()
 
         private void AddShellItemsToMenu(List<ContextMenuFlyoutItemViewModel> shellMenuItems, Microsoft.UI.Xaml.Controls.CommandBarFlyout contextMenuFlyout, bool shiftPressed)
         {
+            var openWithSubItems = ItemModelListToContextFlyoutHelper.GetMenuFlyoutItemsFromModel(ShellContextmenuHelper.GetOpenWithItems(shellMenuItems));
             var mainShellMenuItems = shellMenuItems.RemoveFrom(!App.AppSettings.MoveOverflowMenuItemsToSubMenu ? int.MaxValue : shiftPressed ? 6 : 4);
             var overflowShellMenuItems = shellMenuItems.Except(mainShellMenuItems).ToList();
 
@@ -649,6 +650,22 @@ private void AddShellItemsToMenu(List<ContextMenuFlyoutItemViewModel> shellMenuI
                     overflowItem.Visibility = Visibility.Visible;
                 }
             }
+            
+            // add items to openwith dropdown
+            var openWithOverflow = contextMenuFlyout.SecondaryCommands.FirstOrDefault(x => x is AppBarButton abb && (abb.Tag as string) == "OpenWithOverflow") as AppBarButton;
+            if (openWithSubItems is not null && openWithOverflow is not null)
+            {
+                var openWith = contextMenuFlyout.SecondaryCommands.FirstOrDefault(x => x is AppBarButton abb && (abb.Tag as string) == "OpenWith") as AppBarButton;
+                var flyout = new MenuFlyout();
+                foreach (var item in openWithSubItems)
+                {
+                    flyout.Items.Add(item);
+                }
+
+                openWithOverflow.Flyout = flyout;
+                openWith.Visibility = Visibility.Collapsed;
+                openWithOverflow.Visibility = Visibility.Visible;
+            }
         }
 
         protected virtual void Page_CharacterReceived(CoreWindow sender, CharacterReceivedEventArgs args)
diff --git a/Files/Helpers/ContextFlyoutItemHelper.cs b/Files/Helpers/ContextFlyoutItemHelper.cs
index 97038ade4c4f..0d2914987f04 100644
--- a/Files/Helpers/ContextFlyoutItemHelper.cs
+++ b/Files/Helpers/ContextFlyoutItemHelper.cs
@@ -60,7 +60,7 @@ public static async Task<List<ContextMenuFlyoutItemViewModel>> GetBaseContextShe
         public static List<ContextMenuFlyoutItemViewModel> Filter(List<ContextMenuFlyoutItemViewModel> items, List<ListedItem> selectedItems, bool shiftPressed, CurrentInstanceViewModel currentInstanceViewModel, bool removeOverflowMenu = true)
         {
             items = items.Where(x => Check(item: x, currentInstanceViewModel: currentInstanceViewModel, selectedItems: selectedItems, shiftPressed: shiftPressed)).ToList();
-            items.ForEach(x => x.Items = x.Items.Where(y => Check(item: y, currentInstanceViewModel: currentInstanceViewModel, selectedItems: selectedItems, shiftPressed: shiftPressed)).ToList());
+            items.ForEach(x => x.Items = x.Items?.Where(y => Check(item: y, currentInstanceViewModel: currentInstanceViewModel, selectedItems: selectedItems, shiftPressed: shiftPressed)).ToList());
 
             var overflow = items.Where(x => x.ID == "ItemOverflow").FirstOrDefault();
             if (overflow != null)
@@ -478,6 +478,7 @@ public static List<ContextMenuFlyoutItemViewModel> GetBaseLayoutMenuItems(Curren
                 {
                     Text = "ContextMenuMoreItemsLabel".GetLocalized(),
                     Glyph = "\xE712",
+                    Items = new List<ContextMenuFlyoutItemViewModel>(),
                     ID = "ItemOverflow",
                     Tag = "ItemOverflow",
                     IsHidden = true,
@@ -509,10 +510,21 @@ public static List<ContextMenuFlyoutItemViewModel> GetBaseItemMenuItems(BaseLayo
                     Text = "BaseLayoutItemContextFlyoutOpenItemWith/Text".GetLocalized(),
                     Glyph = "\uE17D",
                     Command = commandsViewModel.OpenItemWithApplicationPickerCommand,
+                    Tag = "OpenWith",
                     CollapseLabel = true,
                     ShowItem = selectedItems.All(i => i.PrimaryItemAttribute == Windows.Storage.StorageItemTypes.File && !i.IsShortcutItem),
                 },
                 new ContextMenuFlyoutItemViewModel()
+                {
+                    Text = "BaseLayoutItemContextFlyoutOpenItemWith/Text".GetLocalized(),
+                    Glyph = "\uE17D",
+                    Tag = "OpenWithOverflow",
+                    IsHidden = true,
+                    CollapseLabel = true,
+                    Items = new List<ContextMenuFlyoutItemViewModel>(),
+                    ShowItem = selectedItems.All(i => i.PrimaryItemAttribute == Windows.Storage.StorageItemTypes.File && !i.IsShortcutItem),
+                },
+                new ContextMenuFlyoutItemViewModel()
                 {
                     Text = "BaseLayoutItemContextFlyoutOpenFileLocation/Text".GetLocalized(),
                     Glyph = "\uE8DA",
@@ -804,6 +816,7 @@ public static List<ContextMenuFlyoutItemViewModel> GetBaseItemMenuItems(BaseLayo
                 {
                     Text = "ContextMenuMoreItemsLabel".GetLocalized(),
                     Glyph = "\xE712",
+                    Items = new List<ContextMenuFlyoutItemViewModel>(),
                     ID = "ItemOverflow",
                     Tag = "ItemOverflow",
                     IsHidden = true,
diff --git a/Files/Helpers/ItemModelListToContextFlyoutHelper.cs b/Files/Helpers/ItemModelListToContextFlyoutHelper.cs
index e595f84077d5..0acb46055b7b 100644
--- a/Files/Helpers/ItemModelListToContextFlyoutHelper.cs
+++ b/Files/Helpers/ItemModelListToContextFlyoutHelper.cs
@@ -14,6 +14,11 @@ public static class ItemModelListToContextFlyoutHelper
     {
         public static List<MenuFlyoutItemBase> GetMenuFlyoutItemsFromModel(List<ContextMenuFlyoutItemViewModel> items)
         {
+            if(items is null)
+            {
+                return null;
+            }
+
             var flyout = new List<MenuFlyoutItemBase>();
             items.ForEach(i =>
             {
@@ -70,7 +75,7 @@ private static MenuFlyoutItemBase GetMenuFlyoutItem(ContextMenuFlyoutItemViewMod
                     Text = item.Text,
                     Tag = item.Tag,
                 };
-                item.Items.ForEach(i =>
+                item.Items?.ForEach(i =>
                 {
                     flyoutSubItem.Items.Add(GetMenuItem(i));
                 });
@@ -153,7 +158,7 @@ private static MenuFlyoutItemBase GetItem(ContextMenuFlyoutItemViewModel i)
             return flyoutItem;
         }
 
-        private static ICommandBarElement GetCommandBarItem(ContextMenuFlyoutItemViewModel item)
+        public static ICommandBarElement GetCommandBarItem(ContextMenuFlyoutItemViewModel item)
         {
             return item.ItemType switch
             {
@@ -185,7 +190,7 @@ private static ICommandBarElement GetCommandBarButton(ContextMenuFlyoutItemViewM
             }
 
             MenuFlyout ctxFlyout = null;
-            if (item.Items.Count > 0 || item.ID == "ItemOverflow")
+            if ((item.Items is not null && item.Items.Count > 0) || item.ID == "ItemOverflow")
             {
                 ctxFlyout = new MenuFlyout();
                 GetMenuFlyoutItemsFromModel(item.Items).ForEach(i => ctxFlyout.Items.Add(i));
diff --git a/Files/Helpers/ShellContextMenuHelper.cs b/Files/Helpers/ShellContextMenuHelper.cs
index 7051beb9393e..d5b51b6e5fde 100644
--- a/Files/Helpers/ShellContextMenuHelper.cs
+++ b/Files/Helpers/ShellContextMenuHelper.cs
@@ -117,6 +117,7 @@ public static void LoadMenuFlyoutItem(IList<ContextMenuFlyoutItemViewModel> menu
                     {
                         Text = menuFlyoutItem.Label.Replace("&", ""),
                         Tag = (menuFlyoutItem, menuHandle),
+                        Items = new List<ContextMenuFlyoutItemViewModel>(),
                     };
                     LoadMenuFlyoutItem(menuLayoutSubItem.Items, menuFlyoutItem.SubItems, menuHandle, showIcons);
                     menuItemsListLocal.Insert(0, menuLayoutSubItem);
@@ -162,5 +163,12 @@ await connection.SendMessageAsync(new ValueSet()
                 return (null, null);
             }
         }
+
+        public static List<ContextMenuFlyoutItemViewModel> GetOpenWithItems(List<ContextMenuFlyoutItemViewModel> flyout)
+        {
+            var item = flyout.FirstOrDefault(x => x.Tag is ValueTuple<Win32ContextMenuItem, string> vt && vt.Item1.CommandString == "openas");
+            flyout.Remove(item);
+            return item?.Items;
+        }
     }
 }
\ No newline at end of file
diff --git a/Files/ViewModels/ContextMenuFlyoutItemViewModel.cs b/Files/ViewModels/ContextMenuFlyoutItemViewModel.cs
index efb0eaf0ea83..3dc08a977e61 100644
--- a/Files/ViewModels/ContextMenuFlyoutItemViewModel.cs
+++ b/Files/ViewModels/ContextMenuFlyoutItemViewModel.cs
@@ -18,7 +18,7 @@ public class ContextMenuFlyoutItemViewModel
         public object Tag { get; set; }
         public ItemType ItemType { get; set; }
         public bool IsSubItem { get; set; }
-        public List<ContextMenuFlyoutItemViewModel> Items { get; set; } = new List<ContextMenuFlyoutItemViewModel>();
+        public List<ContextMenuFlyoutItemViewModel> Items { get; set; }
         public BitmapImage BitmapIcon { get; set; }
 
         /// <summary>