TV Episodes are checked on Itunes, but won't convert to Ipod

I bought 9 episodes of "The Office" for my Ipod this summer. All of a sudden that past 3 months only the first episode will appear on my Ipod. I tried to uncheck and update then recheck and update and nothing. These episodes just will not go back on my Ipod.
I was told if I went to edit and clicked preferences to do auto update all videos then click get videos it would work. However when I did this I can't find auto update under preferences.
Is there anyway I can get these checked episodes actually back and working on my Ipod?
Thanks for all the help!!!!

See if these help:
Updating iPod
http://www.info.apple.com/kbnum/n60944
Can't transfer videos to iPod
http://www.info.apple.com/kbnum/n301461

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