Itunes manually loaded CDs

See Move your iTunes library to a new computer - Apple Community.

tt2

I, too, have this issue. Mine began when I had to restore from a backup after getting a new integrated mb from Apple installed on my MacBook Air as it wouldn't power up. I upgraded the OS and then installed everything from a recent backup. However, I was never able to fully get the iTunes music reloaded on the new system.

I've been going thru Sync'ing and doing it manually from the iTunes Music folder. Even so, there are some pieces of music which Apple Music/iTunes just doesn't have on their library anymore (if they ever did). Most of the music on our system is from our CD collection which we recently sold or let our son have. Some of these pieces will be gone forever.

However, we have an old '09 MacBook which has almost all of what we're missing.

Apple Music on the new system can access old iTunes files as I've pointed Music to an iTunes directory. I can do it manually using the new system syncing features (highlight the grayed out piece, hit Control and click on the piece and then scroll down to the end of the popup and in Finder, locate the piece of music and then double click it to play it; this allows the piece to appear in the Music list and plays. You can even do it with a list and then use Command-O to open the selected pieces which plays the last one selected and they suddenly appear in the Music list in the Music app.)

That process is tedious to say the least. I will likely do it for as many as I can locate and then copy from the old MacBook to the new system those which I cannot locate on the new system under its iTunes directory. I would imagine that I will then, with the copied files, have to go through the same process above, but also copy over the album covers and anything else which might be needed.

Not sure at all how to do this within the Apple Music app so everything is in the correct place.

Any clues to avoid using the terminal app and command line Linux/OSX commands like rsync (similar to rcp?) are appreciated (it's been way too long for me in using any skills I once had doing OS work with Linux.)

Do you have a subscription to either Apple Music or iTunes Match? What changed between now and the last time your library worked correctly? E.g. new computer, upgraded operating system, etc.

tt2

This didn’t work for me and all the music that I ripped from an old pc is slowly going Grey over time. I know longer have the music smh