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Helpful answers
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Jun 9, 2014 3:57 AM in response to elmoelanaby lllaass,iTunes: May be unable to transfer videos to iPhone, iPad, or iPod
iTunes: Frequently asked questions about viewing and syncing videos
If necessary, use a third-party converter like the free HandBrake program.
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Jun 9, 2014 5:08 AM in response to elmoelanaby kanyejosh,This issue is usually caused by incompatible codec in your MP4 container file.
You may use a video converter like AppGeeker (www.appgeeker.com) to convert the video with correct codec like h.264, mpeg-4 that iPod accepts well.
BTW, the utility has iPod profile built in that you can use to simplify the process of choosing codec and other output settings.