New
#11
LOL, tru dat.
I came back to this thread because I had the same problem and couldn't remember what the cryptic procedure was to fix it. But it's still incredibly annoying that once the menu has filled up with about 10 items, Windows does not update that list with recent items - the old stuff from many months ago just stays there until I go through the Taskbar > Properties > Start Menu > uncheck the Privacy options, Apply, then recheck them (I have to do this procedure twice for it to have any effect).
Might there be some clever way to force Windows to show Recent Items in this recent items list, rather than Ancient Items That You Have Not Accessed For Months?