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Stolen from another thread:
"One point I noticed is that if you have your music on your iPhone/ipad streamed through iCloud but not actually downloaded on the device, it's not going to play through the USB cable. It would play through Bluetooth though.
The only way to have the music play through the USB cable is to have it downloaded on your apple device through iTunes or by hitting the iCloud sign next to the song on your apple device. I did it through the regular charging cable."
The Bluetooth aspect probably doesn't apply.
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