ITunes to iPod Video transfer issues

Hi there
I've been having some trouble transfering a specific video file from itunes onto my iPod. It's in the proper format and is in my itunes video library (and plays fine there) but it simply won't do the automatic transfer to the ipod. I've tried deleting the file and reconverting the original source file(an mpeg) into the ipod format, but still no luck.
The weirdest part is that the file is part of a television series, and every other episode of the series transfers fine, this one simply doesn't register.
Thanks in advance for any help, this problem really is getting frustrating.

Do you get an error message saying that some of the files cannot be transfered, blah,blah,blah ?
Does the message bar in itunes tell you a file is being transfered?
Perhaps the file is transfered over-just not where you think it should be....have you checked the recently added playlist under videos?

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