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Helpful answers
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Jul 31, 2016 6:04 AM in response to abschwartzby Mario Mullins,To my knowledge iTunes only syncs music purchased from the iTunes store. To get music from other places on other devices you have to manually sync it.
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Jul 31, 2016 6:15 AM in response to abschwartzby elcpu,I have purchased music (mp3s) from other sources like Amazon and have them in my iTunes library (both Mac and PC). I can sync those back to my iPhone and iPad without issues so it is doable. In fact they behave like all others. I do a manual sync of any music I want using iTunes. The instructions below may help.
Move content from iTunes on your computer to your iPhone, iPad, or iPod touch - Apple Support