iTunes 9: Smart Playlist not syncing as expected

Resolution

If the Smart Playlist on the device is not in the same order as shown in iTunes:

1. Click the Smart Playlist.
2. Set the sort order and arrange as desired.
3. Right-click the Smart Playlist and choose Copy to Play Order.
4. Sync the device with iTunes.

If the above steps do not resolve the issue, continue with the steps listed below. 

If the Smart Playlist on the device does not have the same content as shown in iTunes:

If the Smart Playlist content is all the same kind of media (for example, all music and no videos), try these steps:

1. Right-click the Smart Playlist and choose Edit Smart Playlist.
2. Click the "+" button to create a new rule.
3. Add a new rule with the following selections: Media Kind > Is > Music (or the specific media type for that playlist, such as Podcast, Voice Memo, Audiobooks, and so on).
4. Click OK.
5. Sync the device with iTunes.

If the above steps do not resolve the issue, continue with the steps listed below.

1. Right-click the smart playlist and choose Edit Smart Playlist.
2. Deselect the option for "Live updating."
3. Click OK.
4. Sync the device with iTunes.
5. Check to see if the issue is resolved. If not, proceed to step 6.
6. Click the Smart Playlist.
7. Choose Edit > Select All.
8. Choose File > New Playlist from Selection.
9. Enter a name for the playlist.
10. Click the device on the left-hand side of iTunes.
11. Click the Music tab and then click the new playlist you just named; there should be a checkmark next to the playlist.
12. Sync the device with iTunes.