This is driving me up the wall.
When I'm at home, I generally listen to my music on "shuffle by album" mode, which until Tahoe, worked exactly as expected: Turn on Shuffle, make sure that the "by album" choice was selected in the Controls > Shuffle menu, and…that's all it took. I would often start music playing just by double-clicking the "Albums" item under Library in the left-hand sidebar; Music would then randomly choose an album, play it through, and then move on to the next randomly chosen album.

Or, at least, that's what I used to do. Since Tahoe, not only is this broken, but shuffle itself appears to be severely broken. I ranted about this on my blog, but to recap here:
- If music is not playing, it's impossible to turn shuffle on. Going to the Controls > Shuffle menu shows the options, and you can click on "On", but then when you go back to the menu to check, it's back to "Off". Clicking on the "crossed arrow" shuffle icon in the player control bar does nothing; it's greyed out and doesn't respond to clicks.
- If you start something (an album or track) playing manually, once music is playing, then you can turn on the shuffle option, either through the menu or with the icon in the player control bar. However, if Music is set to "shuffle by album", it plays through the album, but when it reaches the end of the album, it just stops. If you set the menu to "shuffle by song" (Controls > Shuffle > Songs), it…doesn't. It just goes to the next song on the album.
- If I go to the Songs listing, Music _always_ starts with the same song…and honestly, I'm not sure why it's choosing that song. The song in question (not listed here, because it really doesn't matter) isn't the first track with any sort that I can configure. It's not alphabetically first by song title, artist name, album name, or any combination of the above; I have older and newer music…as far as I can tell, Music just decided "this is the first track I'm going to play", and that's it. It is _always_ the first track that Music starts playing unless I specifically tell Music to play some other track.
- Shuffle doesn't. No matter what I do, no matter how I start it playing anything, it plays the next track on the album or playlist. I've occasionally somehow stumbled into a magical world where "shuffle by song" actually starts doing what it's supposed to do, but God only knows how, and even She is guessing.
I know that the Apple Music streaming service is getting all of the attention right now, but I'm absolutely baffled that Apple has managed to break what once was a very nice app for playing the music that I own.
(And as a further grumpy aside, why in the world did y'all have to name the app for paying music Music, and name the service for streaming music Music? It makes talking about all of this so much more difficult. If I'm talking about "Music", is it music generally, the app, or the service? If I say "Apple Music", does that mean I'm talking about the "Apple Music" service, or that I'm specifying the "Apple Music" app? This is getting to be as bad as Microsoft Teams, which calls its groups Teams, so I end up having a work meeting with my team in my team's Team in Microsoft Teams. Nothing about any of this actually has to be this difficult.)