Windows-1 64-bit Home, 20H2
I don't know whether this is an issue with any specific version of Windows, but since the 20H2 update I chose to remove all my apps pinned to the taskbar and pin them to the start menu.
This is actually quite nice - I have 1 more action (invoke start menu) before clicking an app, but this is more than made up for by the greater space (hence navigability) of the start menu (if well organised) than that of the taskbar.
However, I have noticed that some applications, notably (but not exclusively) VMWare Workstation Player 16, Zotero, Veracrypt, Picassa 3) show only generic "dog-eared document" icons in the taskbar when launched form the start menu.
Icons can be persuaded to appear by pinning and then unpinning such anonymous apps from the taskbar.
What is causing this problem and is there a fix? NB icon caches were recently cleared but that has made no difference to the issue
Update A missing icon also reappears/disappears as the Taskbar setting Combine taskbar buttons is switched between Always Hide and Never