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There is no way to lift the 90 day hold without contacting Apple support. You might not get much traction there, but it's worth a try. https://support.apple.com/en-us/HT204074 Turning on iTunes Match, Family Sharing, or Automatic Downloads, or when you download past purchases on your computer, iPhone, iPad, or iPod touch, that device becomes associated ...


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Figured this one out myself: Re-disabled iTunes via Play Button ITunes Patch This (while still stopping iTunes from eating the play button) now makes iTunes launch normally again.


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Check your sync settings. If all music is set to sync it should work out. Another possibility is that they haven't been downloaded yet. In that case a small cloud should be next to the songs in your library. When you click it, they're downloaded.



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