Apple Music only shuffles the first 100 songs on a playlist
When I press shuffle on my playlist (on IOS and web), only the first 100 songs listed get shuffled. Then, once these 100 songs are played, the queue ends. I press 'shuffle', and check the queue. The first 100 songs exactly are shuffled, and any songs past the hundredth don't get played. It doesn't matter what order my playlist is in either, I move all the songs around and the new first 100 are played, followed by nothing else.
This basically softcaps the amount of songs in a playlist to 100 for me, because I don't listen to playlists in order.