Are you refering to the playlist or the songs in your library list? The latter will only play one by one. However I tried it out on both mac & windows & it played thru to the next song without problem, even when I changed windows to search window & then had the program hidden behind the browser. On the mac I didn't even need to highlight the songs in the playlist for them to continue their progresson to the next in line. However if I double-clicked the song from the library then it only played that song. May I recommend rather than double-clicking the song in order to play it, that you instead use the play button. Highlight the which song you wish to play in the playlist & then press the play button.