Certain video will not automatically sync

I have converted an entire TV series to MPEG 4 format. All of the episodes except for the first will automatically sync to the iPod. I can manually add the episode and it transfers fine to the iPod. However, if I change back to automatic sync the episode is removed. The file is checked in the video library on iTunes. I have also tried changing the name of the video. What am I possibly doing wrong?
Sony Vaio   Windows XP  

Rightclick the video in question, hit "Get Info" and make sure the info matches to the others, like if you goto the "Video" tab and see it says "Movies" or "TV SHow" on all the videos THAT DO AUTO UPDATE that it says the same on the one that doesn't auto update

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