@gliebig - Does this happen when the double-playing track is played within a playlist - or when it's played as a single track?
I discussed this with our devs and support team - and no one could come up with a good explanation. One possibility could be a bug involving "pause between tracks" and the "night mode" option to force play on wake. have you enabled either pause between tracks or night mode?
Also - I highly recommend becoming familiar with making playlists. It's very easy to make them: Library> Playlists> hit the "+" ...