iTunes is gone but there are a few simple steps to backing up and restoring an iPod to MacOS Catalina without having to purchase software. You can complete the following steps by using tools that are included for free on your Mac.
In my case I had to back up a really old 1st generation iPod Nano that hadn’t been backed up in years, and restore the files to a 2015, 7th Generation Nano. NOTE: I haven’t tried the steps below with the latest generation iPods (post-7th Gen) or iPhone/iPad.
Also, if you tried to use old command line tricks for running your backups like I did, those won’t work out-of-the-box anymore because the latest MacOS updates include System Integrity Protection (SIP). You can disable SIP, but there’s an easier way! Read on…
Before you get started make sure your Mac is updated to the latest version.
Step 1: Connect iPod to your Mac
Make sure the iPod is on and when you connect it to the Mac by USB cable. Within a few seconds you should see two listings appear in the Finder’s sidebar with the name of your iPod under Locations. If the listings don’t appear the most likely culprit is a bad cable, so you’ll need to try another one.
One of the listings provides an overview of iPod management options, the other listing will let you browse the iPod’s filesystem. In the management listing under the General section I chose to manually manage my music, movies and TV shows. This is important if you don’t want the iPod to automatically sync as soon as you connect it to the Mac.
Step 2: View hidden directories on the iPod
In Finder using the listing that lets you browse your iPod’s filesystem, if you don’t see the iPod_Control directory then you’ll need to unhide file folders. From your keyboard do command + shift + . (that last item is a period on your keyboard) and now you should be able to see all hidden directories including iPod_Control.
Step 3: Copy files from iPod to Mac
Now open another Finder window and create a new directory such as /Documents/iPod_music/.
Copy the iPod_Control/Music/ sub-directory from the original Finder window to the new one. Depending on how many music files you have this could take a while.
Step 4: Sync the Music App
Open Music.app on your Mac. You should see your iPod listed under devices. If not then go back to Step 2.
In the top menu bar go to File > Import and select the directory that has your newly copied music files and then press the “open” button. This should import the files so that they are now managed by the Music app.
Step 5: Restore existing iPod or update new iPod
Once the file import in Step 4 is complete, then you can right click on your device name in the Music app and select sync. When the sync is complete, right click on the device name and choose eject. Once the device has finished ejecting you should now be able to browse and play your files!
Extra Credit
For extra credit, in Finder select the listing that lets you manage the iPod settings run Check for Update. I was surprised there was indeed an update for my Nano.