It has become increasingly annoying that my smart playlists from iTunes do not sync properly with my iPhone. As it turns out, this is a known issue to Apple and they have been, or possibly not, trying to fix this since the beginning of 2009.
After writing a bloody feedback rant to Apple, I also contacted Steve Jobs, quite bluntly in fact, (at an email address I do not know if it is his):
Subject: iPhone Smart Playlists Sync Bug
This issue is known for quite a while now and I am honestly getting sick about it not being resolved.
Would be great if a fix could be rolled out this week.
I doubt he will actually answer, but wouldn’t it be great if a fix would actually be pushed out in the coming week. Hope…
If I do not see an update in the next week, I will walk into the Apple Store and request that I get my money back. And I will get it back.
Update: After playing with iTunes, I found a fix which seems to work … at least partly. For the smart playlists that you want iTunes to sync, turn off the Live Updating in the playlist settings.

