Why won't my shuffle function work properly this has been an ongoing issue

[#1]

On larger Playlist the shuffle function does not properly randomize song selection and instead often plays the same songs whenever I shuffle

[Ximzend]

Yes, I've read about this problem multiple times.

I often use the website Sort Your Music.

After you've chosen a playlist, you can randomize the playlist by clicking on top of the last column called Rnd. Additionally, you can click on A.sep to separate tracks from the same artist.

Then, after you've saved the list, you can play the randomized playlist in that order from beginning to end.