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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 ...


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.


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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