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iTunes is very picky about what kind of formats can be imported into it,  and only a few of media formats are supported by iTunes, including MOV and MP4. So you will need to convert MKV to iTunes compatible format for syncing across multiple devices easily.

If you've discovered how frustrating it is to import MKV files to iTunes, you can get the perfect solution in this article. iTunes cannot play MKV format videos. So you can’t import MKV to iTunes directly, let alone play MKV in iTunes or sync to Apple products like iPhone, iPad, iPod or Apple TV for playback. To import MKV to iTunes, we need to convert MKV to iTunes compatible format first with the help of MKV to iTunes Converter. This guide will take you through the steps of MKV to iTunes conversion.