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[BryanC]

If I add tracks to a playlist while the playlist is currently playing, the playback engine will skip them. Is there any way to change this behavior so it will play the track I place somewhere after the currently playing song in the playlist?

[MrC]

I think the contents of the playlist are added to/replace the Playing Now playlist.  This is the playlist that would need to be updated, so you'd have to add the files there too.