I have tried the suggestions from other threads as to how to fix the issue, but none of these have actually worked. My problem exists with smart playlists. They appear as they should in iTunes playlists and when you look at the playlists within iPhone when it is connected. However, iPhone simply does not recognize the track order. Is this soundling like a bug in the software?
This seems to be a very common problem, and has happened to me at nearly each big iPod/iPhone update for years. It will hopefully be fixed in the next update.
The only fix that has worked for me is unchecking "Live updating" in the Smart Playlist. I need to periodically turn the live updating back on (to update the playlist) and then back off again (to have it properly sync with my phone). I still have some trouble with smart playlists based on other smart playlists, but I'm just living with that for now.
I have a slightly different problem. I have a few artists "Greatest Hits" albums, My iPohone's "iPod" doesn't know the difference between each album. For example:
Queen's Greatest Hits, Guns 'N' Roses Greatest Hits and Alice Cooper's Greatest Hits are all jumbled together into 1 "album" this is fine sometimes gives a bit of variety, but some days i just want to listen to GNR or Queen or Alice Cooper.
The only way to do this is to go in through the "Artist's" Tab instead of "Albums" still, it is annoying.
I don't know why it doesn't work right, but i found a post on a blog with the solution. Right click on the smart playlist and choose "edit smart playlist"-- add another rule that states "playlist...is...music." Sync your phone and it should work. Add this rule to any smart playlists that aren't working, and you can keep live update on as well.