iTunes has 2 taskbar icons when pinned and open. Upinning does not work, they are both identified as the same program.
I frequently use the iTunes toolbar (the little player that sits on your taskbar). However, yesterday I brought iTunes out of its toolbar mode and was horrified to find that it had made a separate icon on my taskbar, and the one pinned to my taskbar was dormant.
I tried the usual "unpin the original icon and pin the new one" trick, but to no avail. They're both identified as the same, and both give me the option to unpin.
I'm running Windows 10, if that helps (although I doubt this is an issue with Windows 10 specifically).