VLC 2.0.6 random playback

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Hello there,
I have a little issue with VLC(ever since I used it):
When ever I enable random playback of music titles it often stops playing just after a few tracks, meaning that not every track on the playlist gets played.
Sometime it already stops after just one track.
This is kinda bothering me as I put stuff in my playlist to be played and not just skipped.

Any ideas why this happens?

Thanks in advance!