Q: I subscribed to iTunes Match for all of my music. I have a number of Smart Playlists where I include only the songs that have not been played in the last 45 days. How are these handled with iTunes Match? When I play a song from this playlist on my iPhone will the song automatically drop off of that playlist, do I need to sync, or is it ignored altogether? I haven’t seen anything posted on this yet and am curious.
A: The good news is that iTunes Match syncs all of your metadata, including things like ratings, play counts and last played dates and times. THis means that the information for your Smart Playlists is synced to the cloud and becomes available on all of your devices.
Smart Playlist updating, however, is a slightly more complicated issue, as live updating of Smart Playlists has been at least somewhat broken on iOS devices for a few years now. This means that with a standard music library synced directly from iTunes, not all of your Smart Playlists will update in the manner that they should; there are several threads in our iLounge Forums discussing this issue, and sadly it is has not really been fixed even in iOS 5.
The good news, however, is that iTunes Match and iCloud seem to do a better job of handling Smart Playlist updating on Apple’s iCloud servers. Synchronization with iCloud is automatic provided you have an active data connection, so as long as you’re online you should see your Smart Playlists update properly, although it may sometimes take a minute or two to synchronize the changes with iCloud. Unfortunately, while listening to your music offline, you’ll still be relying on iOS’ own ability to update your Smart Playlists, in which case your mileage will vary depending on how complex those playlists are. Your metadata and playlists will synchronize with iCloud once you do return to data coverage, however, at which point everything should update correctly.
One important caveat to all of this: Apple has not yet worked all of the bugs out of iTunes Match, so the above describes how things should work under normal conditions. Unfortunately, with iTunes Match being in its early release stages, it is not uncommon to see scenarios where information doesn’t sync properly with iCloud, in which case Smart Playlists will not update properly either.