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 whic ...
Source: http://feeds.macosxhints.com/click.phdo?i=3467862bd1bcf2ed4d437a8278491973
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