1) Make a playlist
2) Add two songs to the playlist
3) Double click the first song in the playlist to begin playing
4) Go back to your library
5) Add a new song to your newly created playlist (do not switch to the play, just drag the track from your Library to the playlist)
6) Skip to the next track. Plays second track in playlist.
7) Hit next again, it goes back to the first track.

This is problematic for I have two screens, and a single playlist for the night. People come up, search the library and just drag their song over to the nightly playlist. But the playlist doesn't recognize their newly added song until you actually switch over to the playlist.