I use Veracrypt to have an encrypted virtual drive, and have pinned shortcuts to portable apps on that drive. Thus, when I first boot up, the shortcuts are invalid, and the icons are just defaults. When I mount the drive, the icons never update to what they should be, even if I right-click the shortcut, go to Properties, and try changing the icon and changing it back, etc.
It used to work in previous versions (the icons would update automatically). I usually only Hibernate, rarely reboot, so if the icons would just update once in a while I'd be golden.