Enabling or re-enabling shuffle during playback causes some strange behaviors.
The active track currently playing continues as usual, but the program displays a random track from the playlist — I'll refer to it as "Song 2" — as being active. Song 2 may be a track that has or has not been played yet. This behavior is reflected in the Main Window's song title area and the Playlist window. My shuffle is configured to play each song in the active playlist once and only once; however, this bug causes Song 2 to be marked as played instead of the original active track. This means that when the playlist has completed, the original active track was played a total of two times, and Song 2 may only have played if done prior to the bug.
I've only been able to replicate this behavior whenever the active track is listed as first in the playlist (prefixed with "1."). I'm using 1.99.16.19516 on Windows 10.