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Can't sync a file to phone for offline play.

Can't sync a file to phone for offline play.

The other day I added two files to a playlist in order to get them to play on my phone. One went over to my phone, the other didn't. I've tried toggling the download, restarting, etc., everything short of reinstalling the app. What else can I do to get this file onto my phone? I've even added other songs to my playlist since then that have worked just fine.

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