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I'm having the same/similar issue. I can't say for certain at what point a song will stop playing, but EVERY song that I've marked for Offline mode will stop playing at least once during the song, and only play again if I manually skip ahead or back in the song. All these songs appear to be already synced. I'm a new premium subscriber. This issue seems like a long term deal killer for me.
That seems to have worked. Thanks.
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