Q: I have recently bought a 5G iPod, and purchased the first season of “The Office” from iTunes. However, when I sync my iPod to the computer it is only transferring one of the six shows.
A: The most common cause of this problem is the actual sync settings in iTunes itself. As explained in our Complete Guide to Managing iTunes Videos, you’ll need to ensure that the iPod synchronization settings for TV Shows are properly configured.
By default, iTunes only synchronizes unwatched videos to the iPod, as determined by the “play count” of the video track. This means that if you’ve watched any of these episodes in iTunes, they will not be transferred to your iPod.
There are also settings in iTunes to sync only recent and recently unwatched TV shows, which might also be affecting how your video content is synchronized to your iPod.
If you have only a few episodes of a show, your safest option is to simply set these settings to sync ALL TV Show content to your iPod.
Should you want to only sync unwatched TV Shows, but want a TV Show you’ve already viewed synced back to the iPod, you can reset the playcount of that particular video track simply by right-clicking on it in iTunes, and choosing the option Reset Play Count. This will set the play count of that track to zero and that episode will then be retransferred to the iPod on the next sync.