Ok I noticed the iPhone must have gotten in a bad state form a previous incomplete sync. Despite deleting all music data on the iPhone, it never recovered via MM.

Eventually, re-syncing via iTunes first and then using MM afterwards seems to have fixed it. I just tried it on one small Auto Playlist and will have to try with my full library and 20+ auto playlists when I get home tonight.

Looks like there is some bug in MM where it can't recover from a previous incomplete sync (perhaps iTunes is able to access/delete/reset some files that MM cannot)

Created a ticket as the forum couldn't handle the length of my log file text:
ETQ-840863

Could you generate debug log (item 4b here: http://www.mediamonkey.com/forum/viewto ... ?f=6&t=341 ) so that we could see why it doesn't work for you?

MM 4.1 build 1670, ios7 iPhone5

When I sync Auto Playlists, the songs 'seem' to be syncing over according to the progress bar but then the songs dont seem to show up on the iPhone. Also the Auto Playlists show up on the iPhone, but are all empty.

If I manually drag and drop files from the explorer view in MM to the iPhone they copy over and are playable but of course no Auto-Playlists this way.

Syncing Auto Playlists seems generally broken for me right now. This all worked flawlessly before with MM 4.0 and ios6