How to make Taskbar app icons right-click remember recent documents?

For years I have pinned apps to the task bar and then, to launch them, I right click on the taskbar icon and I see a list of recent documents I opened with that application. I choose the document and the app launches and opens it. Microsoft Visual Studio is the app I most commonly do this with; As I open different solution files in the app, they start to appear on the list I see when I right click. I can even pin them.

But recently this behavior has simply stopped working. I can open a solution file over and over again and it will no longer appear on the right-click list for the taskbar icon. Older solutions that I previously pinned are still there but no new ones appear.

I suppose I must have changed some Windows setting to make this happen but I have no idea what it is or how to undo it. Is there anyone out there who knows?

I should add that I googled this and found people talking about the group policy editor and a setting called "Do not keep history of recently opened documents" but I checked that setting it has not been configured. So I don't think it is that. Also I went in and checked my "recent items" folder under my user directory and it is completely empty.

Hello,

Double check using the tutorial below to make sure Show recommended files in Start, recent files in File Explorer, and items in Jump Lists is still turned on, and not disabled by policy.