Can't pin files to Word on Taskbar because files don't show up

Question

There was another post from 2022 about not being able to pin frequently used files to the MS Word icon on the Taskbar, but in that case you could right-click on the file name under Recent Files and you would get the option to Pin it. Currently (2025 August) I do not have that option. I was able to Pin files until quite recently so I don't know if this is a bug or a feature that has been discontinued.

Above: right-clicking on the file name under Recent.
There's no option to Pin it, although I can click the star to make it a Favorite.

Above: right-clicking on the MS Word icon in my taskbar.
You can see two other files that I had pinned from some time ago. Despite the fact that I've opened and worked on the file titled "Evidence" quite frequently, it doesn't even show up here as an option to pin.

If making it a Favorite is supposed to replace the Pinned feature, I hope enough people complain about the lost shortcut that it's brought back. If it's a bug that's not working on my system, I hope someone can tell me how to fix it. Thanks in advance!

Answer 1

Dear @Christina

Thank you for posting your question on the Microsoft Q&A forum. I understand your frustration with being unable to pin recent files to the Word icon on your Taskbar.  

Microsoft has recently updated this feature. The traditional "Pin to this list" option inside the Office application's "Recent" list has been replaced by the new "Favorites" feature, which is indicated by the star icon.  

How it is supposed to work now: When you mark a file as a "Favorite" inside Word (by clicking the star), it should automatically appear in the "Pinned" section when you right-click the Word icon on the Taskbar.  

  

Here are the most effective solutions to resolve this.  

Solution 1: Check Windows "Jump List" Settings 

This setting controls the "Recent" and "Pinned" lists for all applications. It may have been disabled. 

1. Open Windows Settings (you can press Windows key + I). 
2. Go to Personalization, then select Start from the left-hand menu. 
3. Ensure the toggle for "Show recently opened items in Start, Jump Lists, and File Explorer" is turned On. 

1. If it is already on, please turn it Off, wait about 10 seconds, and then turn it On again. This action often forces the feature to reset and start working correctly. 

After doing this, open a few files in Word and then right-click the Taskbar icon to see if the "Recent" list is updating and if your "Favorites" now appear as "Pinned." 

Solution 2: Clear the Automatic Destinations Cache 

If the first solution doesn't work, the cache that stores this data might be corrupt. Clearing it will reset the "Recent" and "Pinned" lists for all your applications. 

1. Press Windows + R to open the Run box 
2. Copy and paste the following path into the address bar and press Enter: %AppData%\Microsoft\Windows\Recent\AutomaticDestinations 

1. Delete all the files within this folder. 
2. Restart your computer. Windows will rebuild these files as you use your applications. 

If the issue continues, please consider providing more information: 

• What version of Word are you using? 
• Are any specific files consistently causing this issue? 
• Have you installed any recent updates or changes to your system before this issue started occurring? 

Hope this helps! Let me know if you need any further assistance! 

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