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My files wont transfer from itunes to my ipod classic. What can i do to fix this? Answered

I recently broke my ipod classic. I went and had it replaced with a refrurbished. I registered it and synced my library with it. I noticed a 10 pack of chappelle show that i purchased only having 5 shows come up and into my ipod during the sync even though all were checked. How can i get them all onto it? No matter what i have tried, it just wont upload.

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