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Check the file format of the videos. Certain file formats are unaccepted by iPods.

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Q: Can't drag and drop videos onto ipod nano even with itunes?
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How do you play videos on your iPod?

You have to change your itunes settings. So that you can manage your music/videos. You drag and drop videos into itunes and it will auto sync. (You can only use MP4's) (Video Format)


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