How to Use Open With for Multiple Files on Windows 10

Windows 10 does not reliably show Open with when you select several files at once. The simplest workaround is to add your preferred desktop program to the Send to menu, select the files, and choose that program from Send to. This keeps the normal default file association unchanged and does not require a Registry edit.

Microsoft documents Open With as a Windows Shell verb (the canonical openas verb), and Shell verbs can use different rules for single-item and multi-item selections. That is why a command that appears for one file may disappear for a group of files. See Microsoft's verb selection model documentation for the underlying behavior.

Use Send To as the multi-file Open With workaround

This method works best with traditional desktop applications that can accept one or more file paths when they launch. Text editors, image editors, media players, and similar programs often support this, but support is ultimately controlled by the application.

1. Create or locate a normal shortcut to the app

You only need a regular shortcut to the program. If you already have one on the desktop or in the Start menu, you can reuse it. Otherwise, right-click an empty area of the desktop, choose New > Shortcut, browse to the application's executable, and finish the wizard. Microsoft also documents desktop shortcut creation in its Windows shortcut guidance.

Do not add /a or another command-line switch unless the application's own documentation specifically requires it. The old workaround that appends /a is not a general Windows option; command-line switches are application-specific.

2. Open your SendTo folder

Press Win + R, type shell:sendto, and press Enter. You can also paste that command into File Explorer's address bar. Windows maps this per-user folder to %APPDATA%\Microsoft\Windows\SendTo. Microsoft lists the same location for FOLDERID_SendTo.

3. Copy the app shortcut into SendTo

Copy or move the shortcut you created into the SendTo folder. You can rename the shortcut there to a short, clear label such as Notepad, Photoshop, or VLC. You do not need to change the original application's default-file settings.

Close any open context menu before testing. The new shortcut should appear the next time you right-click a file and open the Send to submenu.

4. Select the files and send them to the app

1. In File Explorer, select the files you want to open. Use Ctrl to pick individual files or Shift to select a range.
2. Right-click one of the selected files.
3. Choose Send to.
4. Select the application shortcut you added.

Why this works, and why some apps fail

For executable drop targets, Windows can convert the selected files into command-line parameters and pass those paths to the application. Microsoft notes that some applications do not accept multiple file names, while others expect a different argument format. The technical details are covered in Microsoft's application registration documentation.

A quick compatibility test is to select two or three files and drag them onto the app shortcut. If the program opens those files, the Send to method should usually work as well. If the app starts but loads no files, or opens only the first file, the limitation belongs to that application's launch behavior rather than to the SendTo folder.

Troubleshooting

• The app is missing from Send to: confirm that its .lnk shortcut is inside shell:sendto, then close and reopen the context menu.
• The app opens but the files do not: remove any unverified command-line switch from the shortcut and test by dragging files onto the shortcut. If that also fails, use the program's own File > Open command.
• You selected a very large batch: Windows intentionally suppresses some context-menu commands for large selections. Microsoft documents a default 15-item threshold for certain commands such as Open, Print, and Edit in its Windows Client troubleshooting article.
• You selected mixed file types: only send files the target application can actually read.

Does this change the default app?

No. This workaround is useful precisely because it is temporary. Double-clicking the files later still uses their normal default application. Use Windows default-app settings only if you want a file type to open in the same program every time.

Windows 10 support note: Microsoft ended standard Windows 10 support on October 14, 2025. Existing PCs continue to run, so this File Explorer technique remains useful, but Microsoft recommends moving to a supported version of Windows or using an eligible Extended Security Updates option during the transition. See Microsoft's Windows 10 end-of-support notice.