diff --git a/src/Files.App/Views/Layouts/BaseLayoutPage.cs b/src/Files.App/Views/Layouts/BaseLayoutPage.cs
index 1813284d66cb..8d5c6acb7f09 100644
--- a/src/Files.App/Views/Layouts/BaseLayoutPage.cs
+++ b/src/Files.App/Views/Layouts/BaseLayoutPage.cs
@@ -216,14 +216,31 @@ public string JumpString
 			}
 		}
 
+		private bool isSelectedItemsSorted = false;
 		private List<ListedItem>? selectedItems = [];
 		public List<ListedItem>? SelectedItems
 		{
-			get => selectedItems;
+			get
+			{
+				if (!isSelectedItemsSorted)
+				{
+					var orderedItems = SortingHelper.OrderFileList(selectedItems, FolderSettings.DirectorySortOption, FolderSettings.DirectorySortDirection, FolderSettings.SortDirectoriesAlongsideFiles, FolderSettings.SortFilesFirst).ToList();
+					selectedItems = orderedItems;
+					isSelectedItemsSorted = true;
+				}
+
+				return SelectedItem is null || !selectedItems!.Contains(SelectedItem)
+					? selectedItems
+					: selectedItems
+						.SkipWhile(x => x != SelectedItem)
+						.Concat(selectedItems.TakeWhile(x => x != SelectedItem))
+						.ToList();
+			}
 			internal set
 			{
 				if (value != selectedItems)
 				{
+					isSelectedItemsSorted = false;
 					selectedItems = value;
 
 					if (selectedItems?.Count == 0 || selectedItems?[0] is null)
@@ -261,7 +278,6 @@ internal set
 
 					NotifyPropertyChanged(nameof(SelectedItems));
 				}
-
 				ParentShellPageInstance!.ToolbarViewModel.SelectedItems = value;
 			}
 		}
@@ -971,7 +987,12 @@ protected virtual void FileList_DragItemsStarting(object sender, DragItemsStarti
 		{
 			try
 			{
-				var shellItemList = SafetyExtensions.IgnoreExceptions(() => e.Items.OfType<ListedItem>().Select(x => new VanaraWindowsShell.ShellItem(x.ItemPath)).ToArray());
+				var itemList = e.Items.OfType<ListedItem>().ToList();
+				var firstItem = itemList.FirstOrDefault();
+				var sortedItems = SortingHelper.OrderFileList(itemList, FolderSettings.DirectorySortOption, FolderSettings.DirectorySortDirection, FolderSettings.SortDirectoriesAlongsideFiles, FolderSettings.SortFilesFirst).ToList();
+				var orderedItems = sortedItems.SkipWhile(x => x != firstItem).Concat(sortedItems.TakeWhile(x => x != firstItem)).ToList();
+
+				var shellItemList = SafetyExtensions.IgnoreExceptions(() => orderedItems.Select(x => new VanaraWindowsShell.ShellItem(x.ItemPath)).ToArray());
 				if (shellItemList?[0].FileSystemPath is not null && !InstanceViewModel.IsPageTypeSearchResults)
 				{
 					var iddo = shellItemList[0].Parent.GetChildrenUIObjects<IDataObject>(HWND.NULL, shellItemList);
@@ -987,7 +1008,7 @@ protected virtual void FileList_DragItemsStarting(object sender, DragItemsStarti
 				else
 				{
 					// Only support IStorageItem capable paths
-					var storageItemList = e.Items.OfType<ListedItem>().Where(x => !(x.IsHiddenItem && x.IsLinkItem && x.IsRecycleBinItem && x.IsShortcut)).Select(x => VirtualStorageItem.FromListedItem(x));
+					var storageItemList = orderedItems.Where(x => !(x.IsHiddenItem && x.IsLinkItem && x.IsRecycleBinItem && x.IsShortcut)).Select(x => VirtualStorageItem.FromListedItem(x));
 					e.Data.SetStorageItems(storageItemList, false);
 				}
 			}
@@ -1176,19 +1197,26 @@ private void RefreshItem(SelectorItem container, object item, bool inRecycleQueu
 			}
 		}
 
-		protected static void FileListItem_PointerPressed(object sender, PointerRoutedEventArgs e)
+		protected internal void FileListItem_PointerPressed(object sender, PointerRoutedEventArgs e)
 		{
 			if (sender is not SelectorItem selectorItem)
 				return;
 
-			if (selectorItem.IsSelected && e.KeyModifiers == VirtualKeyModifiers.Control)
+			if (selectorItem.IsSelected)
 			{
-				selectorItem.IsSelected = false;
+				if (e.KeyModifiers == VirtualKeyModifiers.Control)
+				{
+					selectorItem.IsSelected = false;
 
-				// Prevent issues arising caused by the default handlers attempting to select the item that has just been deselected by ctrl + click
-				e.Handled = true;
+					// Prevent issues arising caused by the default handlers attempting to select the item that has just been deselected by ctrl + click
+					e.Handled = true;
+				}
+				else
+				{
+					SelectedItem = GetItemFromElement(sender);
+				}
 			}
-			else if (!selectorItem.IsSelected && e.GetCurrentPoint(selectorItem).Properties.IsLeftButtonPressed)
+			else if (e.GetCurrentPoint(selectorItem).Properties.IsLeftButtonPressed)
 			{
 				selectorItem.IsSelected = true;
 			}