I have an 80 GB iPod Classic.

Until recently it "just worked" when syncing. Lately it refuses to sync new songs that have been added to iTunes either via CD or the Music Store.

The music is in the iTunes library, I have iTunes set to sync all checked songs and all playlists.

The other day I added a new playlist and then added some newly checked songs (they had been in the library for awhile but were unchecked) and I synced. Unfortunately neither these newly checked songs nor the new playlist showed up on my iPod. A 2nd sync while the iPod was still connected made no change.

As I said earlier, this behavior is the same with newly added songs from CD's or the iTunes Store.

I have discovered a work around. If I create a playlist and select my whole library and import it into that playlist, then the new songs show up.

I would really like to get the intended functionality back.

What would be my best course of action?