Apr 14, '11 07:30:00AM • Contributed by: ckoerner
I've been using them for a few years without problem, then with the release of iTunes 9 (if I recall correctly) they appeared to stop working. The smart playlists and songs were syncing to my iPhone just fine, but not the most recent 50, nor the most recent rated 5 stars. It appeared to be a random selection and I could not figure out what was going on!
Lo and behold, it wasn't anything to do with the new release of iTunes. What had happened is that while viewing my smart playlists in iTunes I had changed the sort order from 'Date Added' to a different column!
When syncing playlists to your iOS device (whether they are 'smart' or not), the order in which you have the playlist sorted by in iTunes will determine how they are displayed on the iOS device. So if you set up a playlist and have it sorted by a column such as 'Plays', 'Tracks', etc that is how they will appear on the iOS device. It can be quite confusing especially when using smart playlists to determine the criteria for the sort order.
[crarko adds: I tested this, and it works as described. Although I tend to manage my media manually rather than auto-syncing.]
