Apple Music library transfer + sync issues (OS 10.15

Here’s some tech problems that I haven’t heard of anyone else having.

I have an extensive music library I’ve collected over the years, which happens to include a lot of obscure music that was never properly released to the public. I created my digital music library with iTunes on my Mac, which was a joy to synchronize with my iPhone. As I would continue to upgrade my devices and expand my music collection, I made sure I could transfer the music library settings to each of my computers. I also made sure that the music would be on a dedicated external hard drive, which was regularly cloned on a backup drive.

With iTunes, I located the settings folder (located at users/ME/Music/iTunes) and would preserve these files in backup date-marked folders featuring what I believed were the essential documents (iTunes Library Extras.itdb, iTunes Library Genius.itdb, iTunes Library.itl and iTunes Music Library.xml). As the iTunes app was replaced by “Music” app, the new essential documents were replaced with a single document (“Music Library”) at a new location (users/ME/Music/Music/Media).

For the most part, It’s been a relatively easy process.  For the past years, I’ve been able to use the same setup for Music (1.0.6.10) on my 2012 MacBook Pro(s) running Mac OS 10.15 as well as Music (1.5.534) Music on my 2023 MacBook Pro running Mac OS 15.5.

At least until recently.

I recently re-configured my secondary 2012 MacBook Pro with a new SSD, and used Migration Assistant to transfer my settings.  Unfortunately the essential Music document (“Music Library”) is not working as it should. It’s not only not working with the Music app (the only music I can see are the Apple purchases - missing quite a few thousand albums), but it’s also grayed-out and cannot removed from the preferences.

Just to make matters worse, my primary 2012 MacBook Pro cannot be synced with my IPhone 14, which it was able to do in the past.  When I plug in the iPhone to the Mac, there is no acknowledgement from the Music application. I can synch the iPhone with Image Capture to download photos, but I can no longer sync with the Music app…. even after trying various lighting cables.

Hopefully someone has some solutions for both of these issues.

- EP