I can't transfer tv show from itunes to ipod

I'm on automatic sync, but a tvshow i purchased won't transfer. It has next to the check/no check box. Then an alert pops up saying unable to find file. I just bought the show from from itunes store. A couple of songs came out this way too. Whats up?

My 13 yr. old daughter solved this problem, and successfully imported the TV show to her Ipod.
She tells me she has no idea how she did it, she just did it.
So, although I guess my problem is solved, I'd still love to know what the answer is.
Later

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