Won't transfer some of videos

I bought a season of a TV show from iTunes recently and when I tried to transfer the videos to my iPod only 3 of the episodes would transfer. They play fine on my iTunes/computer when I attempt to find them and I know there is room on my iPod; however, they will not transfer over. I have transfered other videos over and know that it does work, but why can't I get these specific ones to transfer to my iPod?

For difficulties transferring iTunes purchases, see this.
iPod does not play content purchased from the iTMS.

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