I have been frustrated with the same issue. It definitely has something to do with long songs but doesn’t seem to be consistent. Does seen to happen to songs longer that 10:00, but does not restart at 10:00. I did some testing today and here are the results: Push.it (9:55) played all the way through (sorry, it won't let me use the actual song name) Culling Voices (10:05) restarted at about 6:49 Pneuma (11:53) restarted at 9:00 7empest (15:43) restarted at about 12:44   Edit: Today I had it happen on a song much shorter than 10:00.  Loose Yourself - Live at Civic Theater, Newcastle, Australia (8:14) Restarted at 5:16, right in the middle of "nine to five". ... View more