Smart Playlists are not syncing!

I don't remember when this stopped working but I have 1 playlist that shows in iTunes but does not update on the iPod. Not sure why... all the others seem to sync just fine. Any insight would be greatly appreciated.

Solution/work around:
Add a new smart play list.
File > New Smart Playlist. From this point a pop up will appear.
Match following rule is selected
(Date added) - (In the last) - (2) - (weeks)
No limit set
No match only checked items
Live update selected
Then <ok>.
Change name of smart playlist to something like 'New Music' and Sync to IPhone/IPod.

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