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One movie was a digital download from a DVD insert, one I purchased myself. Neither movie will copy into the Movies section of my iPod when I have it connected. I get no error messages telling me why they will not copy over or anything.
iPod classic 160GB (Late 2009)
Not all iTunes video can be transferred to iPod, please make sure your video is compatible with iPod. If the video resolution or video bit rate beyond iPod Classic limitation, you can't upload them to iPod. For example, some iTunes purchased movie are High definition movie, the resolution is too high to play on iPod Classic, you can
highlight the problem video in iTunes and choose Create iPod or iPhone version from the Advanced drop down menu. When the conversion process has completed, sync the new version to your iPod. Or you may refer to this tutorial that is about how to convert and sync video to iPod.
I just downloaded movies from iTunes and they won't copy onto my iPod.
