diff --git a/src/Files.App/Data/Items/ListedItem.cs b/src/Files.App/Data/Items/ListedItem.cs
index c340a0eb1a90..4968d3d6e211 100644
--- a/src/Files.App/Data/Items/ListedItem.cs
+++ b/src/Files.App/Data/Items/ListedItem.cs
@@ -374,6 +374,7 @@ public override string ToString()
 		public bool IsAlternateStream => this is AlternateStreamItem;
 		public bool IsGitItem => this is GitItem;
 		public virtual bool IsExecutable => FileExtensionHelpers.IsExecutableFile(ItemPath);
+		public virtual bool IsPythonFile => FileExtensionHelpers.IsPythonFile(ItemPath);
 		public bool IsPinned => App.QuickAccessManager.Model.FavoriteItems.Contains(itemPath);
 		public bool IsDriveRoot => ItemPath == PathNormalization.GetPathRoot(ItemPath);
 		public bool IsElevated => CheckElevationRights();
diff --git a/src/Files.App/Helpers/Navigation/NavigationHelpers.cs b/src/Files.App/Helpers/Navigation/NavigationHelpers.cs
index d6cb86a7e012..e718cb75fc5f 100644
--- a/src/Files.App/Helpers/Navigation/NavigationHelpers.cs
+++ b/src/Files.App/Helpers/Navigation/NavigationHelpers.cs
@@ -83,7 +83,7 @@ public static async Task OpenSelectedItemsAsync(IShellPage associatedInstance, b
 
 		public static async Task OpenItemsWithExecutableAsync(IShellPage associatedInstance, IEnumerable<IStorageItemWithPath> items, string executable)
 		{
-			// Don't open files and folders inside  recycle bin
+			// Don't open files and folders inside recycle bin
 			if (associatedInstance.FilesystemViewModel.WorkingDirectory.StartsWith(Constants.UserEnvironmentPaths.RecycleBinPath, StringComparison.Ordinal) ||
 				associatedInstance.SlimContentPage is null)
 			{
@@ -104,6 +104,21 @@ public static async Task OpenItemsWithExecutableAsync(IShellPage associatedInsta
 			}
 		}
 
+		public static async Task OpenItemsWithPythonAsync(IShellPage associatedInstance, IEnumerable<IStorageItemWithPath> items, string pythonScriptPath)
+		{
+			// Don't open files and folders inside recycle bin
+			if (associatedInstance.FilesystemViewModel.WorkingDirectory.StartsWith(Constants.UserEnvironmentPaths.RecycleBinPath, StringComparison.Ordinal) ||
+								associatedInstance.SlimContentPage is null)
+			{
+				return;
+			}
+
+			foreach (var item in items)
+			{
+				await Win32Helpers.InvokeWin32ComponentAsync(pythonScriptPath, associatedInstance, arguments: $"\"{item.Path}\"");
+			}
+		}
+
 		/// <summary>
 		/// Navigates to a directory or opens file
 		/// </summary>
diff --git a/src/Files.App/Utils/Storage/Operations/FilesystemHelpers.cs b/src/Files.App/Utils/Storage/Operations/FilesystemHelpers.cs
index e9b0a3109b35..22fc6d54b7fd 100644
--- a/src/Files.App/Utils/Storage/Operations/FilesystemHelpers.cs
+++ b/src/Files.App/Utils/Storage/Operations/FilesystemHelpers.cs
@@ -231,7 +231,8 @@ public async Task<ReturnResult> PerformOperationTypeAsync(
 			string destination,
 			bool showDialog,
 			bool registerHistory,
-			bool isTargetExecutable = false)
+			bool isTargetExecutable = false,
+			bool isTargetPythonFile = false)
 		{
 			try
 			{
@@ -260,6 +261,12 @@ public async Task<ReturnResult> PerformOperationTypeAsync(
 						NavigationHelpers.OpenItemsWithExecutableAsync(associatedInstance, items, destination);
 						return ReturnResult.Success;
 					}
+					else if (isTargetPythonFile)
+					{
+						var items = await GetDraggedStorageItems(packageView);
+						NavigationHelpers.OpenItemsWithPythonAsync(associatedInstance, items, destination);
+						return ReturnResult.Success;
+					}
 					else
 					{
 						return await CreateShortcutFromClipboard(packageView, destination, showDialog, registerHistory);
diff --git a/src/Files.App/Utils/Storage/Operations/IFilesystemHelpers.cs b/src/Files.App/Utils/Storage/Operations/IFilesystemHelpers.cs
index 083e323b4c2f..204e592b7434 100644
--- a/src/Files.App/Utils/Storage/Operations/IFilesystemHelpers.cs
+++ b/src/Files.App/Utils/Storage/Operations/IFilesystemHelpers.cs
@@ -114,7 +114,7 @@ public interface IFilesystemHelpers : IDisposable
 		/// The <paramref name="destination"/> is NOT fullPath</param>
 		/// <param name="registerHistory">Determines whether <see cref="IStorageHistory"/> is saved</param>
 		/// <returns><see cref="ReturnResult"/> of performed operation</returns>
-		Task<ReturnResult> PerformOperationTypeAsync(DataPackageOperation operation, DataPackageView packageView, string destination, bool showDialog, bool registerHistory, bool isDestinationExecutable = false);
+		Task<ReturnResult> PerformOperationTypeAsync(DataPackageOperation operation, DataPackageView packageView, string destination, bool showDialog, bool registerHistory, bool isDestinationExecutable = false, bool isDestinationPython = false);
 
 		#region Copy
 
diff --git a/src/Files.App/Views/Layouts/BaseLayoutPage.cs b/src/Files.App/Views/Layouts/BaseLayoutPage.cs
index 74ca24f67766..515b3274bf7f 100644
--- a/src/Files.App/Views/Layouts/BaseLayoutPage.cs
+++ b/src/Files.App/Views/Layouts/BaseLayoutPage.cs
@@ -1034,7 +1034,7 @@ private async void Item_DragOver(object sender, DragEventArgs e)
 					{
 						e.DragUIOverride.IsCaptionVisible = true;
 
-						if (item.IsExecutable)
+						if (item.IsExecutable || item.IsPythonFile)
 						{
 							e.DragUIOverride.Caption = $"{"OpenWith".GetLocalizedResource()} {item.Name}";
 							e.AcceptedOperation = DataPackageOperation.Link;
@@ -1112,7 +1112,7 @@ private async void Item_Drop(object sender, DragEventArgs e)
 
 			var item = GetItemFromElement(sender);
 			if (item is not null)
-				await ParentShellPageInstance!.FilesystemHelpers.PerformOperationTypeAsync(e.AcceptedOperation, e.DataView, (item as ShortcutItem)?.TargetPath ?? item.ItemPath, false, true, item.IsExecutable);
+				await ParentShellPageInstance!.FilesystemHelpers.PerformOperationTypeAsync(e.AcceptedOperation, e.DataView, (item as ShortcutItem)?.TargetPath ?? item.ItemPath, false, true, item.IsExecutable, item.IsPythonFile);
 
 			deferral.Complete();
 		}
@@ -1257,7 +1257,7 @@ protected void InitializeDrag(UIElement container, ListedItem item)
 				return;
 
 			UninitializeDrag(container);
-			if ((item.PrimaryItemAttribute == StorageItemTypes.Folder && !RecycleBinHelpers.IsPathUnderRecycleBin(item.ItemPath)) || item.IsExecutable)
+			if ((item.PrimaryItemAttribute == StorageItemTypes.Folder && !RecycleBinHelpers.IsPathUnderRecycleBin(item.ItemPath)) || item.IsExecutable || item.IsPythonFile)
 			{
 				container.AllowDrop = true;
 				container.AddHandler(UIElement.DragOverEvent, Item_DragOverEventHandler, true);
diff --git a/src/Files.Shared/Helpers/FileExtensionHelpers.cs b/src/Files.Shared/Helpers/FileExtensionHelpers.cs
index 1bd0230cbeed..99a7ef93367e 100644
--- a/src/Files.Shared/Helpers/FileExtensionHelpers.cs
+++ b/src/Files.Shared/Helpers/FileExtensionHelpers.cs
@@ -206,5 +206,16 @@ public static bool IsCertificateFile(string? filePathToCheck)
 		{
 			return HasExtension(filePathToCheck, ".cer", ".crt", ".der", ".pfx");
 		}
+
+		/// <summary>
+		/// Check if the file extension is a Python file.
+		/// </summary>
+		/// <param name="filePathToCheck"></param>
+		/// <returns><c>true</c> if the filePathToCheck is a python file; otherwise, <c>false</c>.</returns>
+		public static bool IsPythonFile(string? filePathToCheck)
+		{
+			return HasExtension(filePathToCheck, ".py");
+		}
+
 	}
 }