I have a playlist with over 1500 songs and when I shuffle, it starts playing the exact same songs it did the day before and the day before that...I swear it shuffles only 200 of the 1500 songs. This has been an issue for over a decade and STILL not fixed??
iPhone 15 Pro
For some reason the same suggestion is given for this behavior and that is to make sure the Repeat button is not activated:
Why do all the same songs play on shuffle? - Apple Community
I have not had this issue and listen to my shuffled playlist everyday in my car. I shuffle it every time because I don't want to know what song is going to play next and it never shuffles it to the same songs. Sorry I can't verify the issue you are having, but let us know if shutting off the repeat option makes any difference. The others who have asked the same question never followed up if they found a solution or if this fixed it.
Apple Music shuffles SAME songs all the time
