shortly after updating my watch to os5, i discovered its music player no longer marked tracks played. this had worked in os4 - they busted something in regression. reported my problem to @applesupport who escalated it to a senior support analyst. we went through several iterations before the problem was clearly understood. then the analyst filed a bug with engineering. none of the updates to os5 fixed the bug.
updated my watch to os6. went for a hike, leaving the phone at home. sad to report the bug is still there. only the last track played got marked after the watch synced to the phone and the phone synced to itunes. this is really disappointing because otherwise the watch is a much better source of tunes whilst hiking/running. the phone being bulky, has to be in a pocket and when it’s in there flesh and bone are rather opaque to bluetooth signals and thus annoying dropouts occur.
why is this bug a problem: my strategy is to use a smart playlist that selects by least recently played. after a track is played, it drops off that playlist. thus i get new tracks each time i start the music player.