I've been a long-time user and the one thing that has bothered me throughout each version that I have used is that when you load a new playlist into VLC by right clicking on a folder and adding it to VLC, playing the list and either setting to random then or having it started with "random" by default, not every song is played.
Sometimes the playlist ends after only a few songs, sometimes it ends after two songs. Sometimes it plays all the songs in the list and then stops.
I believe it happens under both Ubuntu and Windows although I've got way more play-time with the latter so I might be mistaken.
Is this a known bug? Am I doing something wrong? I'd assume that if I put my music on "random" that it would play all the songs regardless, not arbitrarily play a few.
This behaviour mostly seems to occur when it's playing the last song before the other songs, usually leaving me with a feeling that the album was shorter than I remembered only to realise VLC quit playing it.