"Random" play doesn't work,stops after each song; multiple plays of same

One of the more annoying things happening: random doesn't work.
I've gone through the Zen Media Explorer, reformated the Zen player, so there were no songs on it.
Went and built a list of 37 songs and uploaded via Zen Media Player to the Zen player.
Went to "Music" and selected "All Tracks"
Set my "System" "Audio Settings" for "random" play.
I had to pick the first song to start it off.
It played the first 5 or so songs correctly.
Then it stopped.
I used the bottom arrow key to "play" the next song. Then it stopped AGAIN.
Now I'm manually making each song play! This goes on for 4-5 songs, then it starts playing automatically - but repeating the songs it has already played. It does not go near the other 28 or so songs that I have not heard yet!
I go back to "Music" and re-set to "All Tracks"
I go back to "System" "Audio Settings" and re-set to play "random"
And it does this annoying routine all over again.
Went back to "System" "Audio Settings" and picked "normal" this time. So of course, its playing all the same songs I've heard over again.
I have to manually cruise the "All Tracks" to pick what I want to hear.
Can anyone help me with this? I can't stand it anymore.

If you installed any software to work with the mouse, remove it according to the developer's instructions, then restart the computer and test. Back up all data before making any changes.

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