Smart List not updating on iPod (Classic)

I've got an iPod Classic with my entire iTunes library syncing to it. I'm running iTunes 11.0.1.12 on Windows 7.

I have a Smart Playlist that I have been using for several years, and until recently, when I sync the playlist to the iPod, it updates while I play music. The Smart Playlist is actually based on another one, but this is basically how it is set up.

"Jamz" is actually another Smart Playlist

So when I play the songs from the "Jams 5 star" playlist, normally once a song has been played, it no longer qualifies for the list, so it gets replaced by a new one. This has been working on my iPod for a long time. However, I recently noticed that it was no longer updating, for me to update the list, I have to now sync the iPod with iTunes.

As I am away from home for work a lot, sometimes for weeks at a time, it is important I get this fixed, but I can't seem to find the problem. I have some other playlists that are working properly on the iPod, this one (and others that are very similar) are not working, and I can't figure out why.

Any help would be appreciated.