"Purchased" playlist it doesn't download

So fairly recently, I tried to sync my iPod touch. However, when I was syncing it my "Purchased" playlist will not sync. It will sync every other playlist but THAT ONE. It is really annoying because all of my new music is on THAT particular playlist. I haven't a clue why it isn't downloading the playlist. Can anyone help?

Do the songs play in iTunes on the computer?
Is there anything different about the songs that do sync and those that do not?
Do you have any Restrictions (Settings>General>Restrictions) set that would prevent syncing those songs? (iTunes purchases only)

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