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What Apple ID are you using? (Does iTunes > Store [menu at the top] > Sign in = CTRL+CLICK on a TV show in iTunes > Get Info > Summary page says what Apple ID it's associated with).
You can always try re-encoding it by right-clicking the file then selecting "Create iPod version" and it will re-encode the show to the proper settings for an iPod.
-=/ Daft Tech /=-