Purchased video from itunes won't transfer to ipod

I bought a tv show on itunes on my old computer (along with some music videos) and transfered all of those plus all of my music to a new computer. The music videos and music updated back onto my ipod, but the tv show did not. Since then, I've been having trouble updating any video that fits the requirements for my ipod. I am able to add it to itunes, but it will not update. I know there's something wrong with either itunes or my ipod (I have updated the software on both) because my cousin was able to add a certain movie to his ipod, but mine won't update it. Does anyone know what's going on?
  Windows XP  

Welcome to Apple Discussions!
Connect your iPod to your computer and when it appears in iTunes go to edit-->preferences. Click the iPod tab. Then hit the video tab. Make sure automatically update all videos is selected.
If it is, then click update no videos at the bottom and hit okay. Eject the iPod. Then connect it back up and reenable the option.
Merry Christmas
btabz

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