I used to be able to pin playlists to Winamp on the Taskbar, so when I right click WinAmp it would show the context menu with my pinned playlists, just like with the explorer folder icon etc. However at some point recently, when I right click on WinAmp it only shows the basic 3 options in the context menu: "Winamp", "Unpin...", "Close..." Winamp itself pins fine to taskbar, but I can't pin playlists to the icon anymore. I tried uninstalling and re-installing, also tried to unpin and "repin" the item but nothing has worked. I also tried to manually remove the shortcut (via "C:\Users\[USER]\AppData\Roaming\Microsoft\Internet Explorer\Quick Launch\User Pinned\TaskBar") but when I add Winamp back to the taskbar, it still won't let me pin a playlist. All my other icons in the taskbar work properly, if I right click on Chrome or Explorer on the taskbar it shows my pinned items. Any ideas?
Fix! I'm responding to my own thread here in case anyone comes across this post in the future via search or whatever. The issue I was describing in my post can be fixed by deleting the contents of this folder: C:\Users\[USERNAME]\AppData\Roaming\Microsoft\Windows\Recent\AutomaticDestinations\ This will reset all the icons on your taskbar and all the context items will be cleared. Now when you pin an item to the taskbar it will appear in the context menu again.