I've had a problem forever now, and just got around to deciding to try and fix it.
Reinstalling the apps makes no difference, and this is affecting multiple apps
The issue is very simple: When I right-click the icon for Pr or Ae on my taskbar (W10), it comes up with a list of my recent files, including any I have pinned at the top.
However, the most recent file... is not there.
I open up Pr, and on the front screen, there are my recent files, and the one I worked on yesterday is at the top of the list. But not when I right-click on my taskbar icon.
I create a new project, save it, close Pr.
Check the taskbar, still nothing, neither the file I worked on yesterday, or the one I just created is there, only the ones I worked on before.
Clearly there is some way to get entries onto the list because I have older files showing there, but never the actual most recent files.
Tried contacting Adobe chat this morning who were next to useless and started to tell me I was using the wrong workflow, and that it takes time for items to appear on the recent files list, which sounded nonsense.