How to run multiple instances of iTunes and or Apple Music on your Mac under a single user account

Like so many I am currently stuck at home due to a pandemic. And I guess like so many I try to keep busy with a bunch of projects. For me one of these project is reviving my iPod Classic 160 GB, I accidentally cleared it because I hooked it up to the wrong Mac. I then realised that I no longer had the iTunes library which I used to sync to my iPod because I threw that thing away when I moved to Apple Music.

Why?

Thinking about how I would want to use both the new world music library and the old one I eventually settled for two separate libraries. For me the whole online Apple Music library combined with my “old on-disk music files” was to confusing. But I guess you can have multiple reasons why you would want to have two instances of iTunes and or Apple Music running under one user.

How?

By default you’re not able to run any of the standard Apple Applications twice. But I started off fiddling with terminal command line arguments. You can launch a new session of most apps using –new. So I tried:

open /system/applications/music.app --new 

Sadly this doesn’t seem to be working for Apple Apps on OS Catalina. My initial goal was to provide this command with an extra argument pointing it to a specific library, and maybe eventually ending op with two aliases. So If anyone at Apple is reading this.. feature request.

My solution:

After my failed attempt I research the interwebs some more and found a project on GitHub by cormiertyshawn895 called Retroactive. This project has been specifically built for running older versions of Aperture, iPhoto and iTunes on newer Apple operating systems like Mojave, High Sierra and Catalina.

I started off by closing Apple Music, and After installing Retroactive and allowing it to run from the “Security & Privacy” preferences menu you can select iTunes to start installing a second all tough being a older version of iTunes on your system.

In the second screen you can select your preferred version of iTunes, as this solution probably won’t last forever I opted for the most recent version.

After finishing up I started iTunes 12.9 pressing my option ⌥ key while doing so. This will trigger a pop-up menu asking you to open an existing library or create a new one. I opted for creating a new library in a new folder structure within my Music folder.

Final thoughts

I ended up with the perfect solution (for me). I turned off Apple Music Library integration in my 12.9 library. I did log onto my iCloud account (same one as in my Apple Music) without any issues. To sync my iPod my method is to have iTunes 12.9 running when I connect it to my Mac, I do get pop-up warning saying my iPod is “in use by other user on this Mac” but I’ve been ignoring this an everything is working fine! as you can see in the image below two instances of in my case Apple Music and iTunes running at the same time.

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