Has anyone noticed since the major update that the play order that you see in itunes does not carry over to the iphone? This is also the case with itunes match. Can't figure out why, but the playlist order should be exactly the same on the phone as you see in itunes. I hope they fix this soon as I like to listen to my most recently added music from the top down and usually sort it in itunes by date added. This does not carry over to iphone. Anyone have a work around?
My playlists duplicate exactly on the iPhone as they are in iTunes. Maybe uncheck the music sync in iTunes and clear the iPhone then check it again and see if it fixes itself. I don't use Match (too much music in my library), but it does seem like it is a bit buggy right now if that is how you are syncing.
iTunes and sync with iPhone definitely has some bugs, I just deleted the playlist and started over, then synced again..I even had to go so far as to completely delete and re-download 1 album that would not sync to my 4S..
This is not new although it might not have affected you in the past. I'm not in front of iTunes right now (I'm sure someone will correct any mistakes I make). With your device plugged in, go to your playlist, right click (Windows) and choose something like copy playlist order (or some wording to that effect). You'll be all set from now on. Future songs will show up correctly.