How do I allow pinning a file (i.e. PDF) to the Start menu?

Question

Hi. I have spent more hours on this than you can imagine.

On my prior Windows 10 Pro computer, I had the options to pin files (i.e. PDF) to the Start menu and/or Taskbar. On my new computer which is running Windows 10 Pro in Hyper-V, I do not have that option. I have checked all group policies; I have also looked at several registry settings, all to no avail. I have read several postings here on Microsoft's Q&A site.

This should be so simple. Does anyone know what I need to set/tweak so that when I right-mouse click on a file, Pin to Start and Pin to Taskbar options are available?

Thank you in advance.

Answer 1

Hello, I’m Henry, happy to help with this.

Since you're in Hyper-V, the base Windows 10 Pro image should behave like a normal installation. The issue is almost certainly related to the standard Windows behavior of not allowing direct pinning of document files, requiring the shortcut workaround for Start or the Jump List method for the Taskbar.

1. Pinning a PDF to the Start Menu

• Open File Explorer and navigate to your PDF file (e.g., E:\path\to\your\file.pdf).
• Right-click on the PDF file → Send to > Desktop (create shortcut).
• Go to your Desktop, where the new shortcut has been created.
• Right-click the shortcut file → Pin to Start.

2. Pinning a PDF to an Application's Jump List on the Taskbar

• Pin the Application to the Taskbar: Ensure the application you use to open PDFs (e.g., Adobe Acrobat Reader, Microsoft Edge, Foxit Reader) is pinned to your Taskbar. If it’s not pinned: Find the application in your Start Menu, right-click it, and select More > Pin to taskbar.
• Open the PDF File: Open the PDF file you want to access frequently using the pinned application.
• Use the Jump List:
  • Right-click the application's icon on the Taskbar (e.g., Adobe Reader icon). Your recently opened PDF will appear in the Recent list.
  • Hover over the PDF file → A pin icon appears to the right. Click the pin icon.
  • The PDF will now be in the Pinned section at the top of the application's Jump List for easy access.

Hope this helps.