[fuzzmz]

It's not really random, in the sense that if you have a playlist and hit shuffle it'll always play in the same order instead of randomizing the play order each time you listen to that playlist. Basically, with the current behavior, once you learned the order of the shuffled songs you can always know what comes next.

[joegahona]

Is there a technical reason it does this, and why it's so difficult to correct?

[tjoff]

Technical debt.