@troublewithwords I’m sorry to hear that… it’s disappointing how Apple has let iTunes/Music languish in service of their streaming offerings. I still use the app to organize and manage my large collection of MP3s here but it’s clear there are tons of bugs and problems with the neglected software. Hopefully you can find a better system.

Note: I’ve seen some open source and alternative ripping softwares you might try as well, but I’ve never used any personally.

@troublewithwords just to check, before you fully give up… when I rip CDs it puts them in the old iTunes Media folder from long ago (instead of the Music app media folder). So it might be worth checking there? I right click on the song in the music app and select “Show in Finder” to help locate the file.

Also, there used to be an app called PhoneView that would let you connect an iPhone and manually sync files, but I haven’t used that in years so I can say if it’s still viable.