iPod Nano will NOT connect to iTunes on Catalina

[magentawave]

ISSUE: My 7th gen iPod Nano will NOT connect to iTunes now after I installed iTunes 12.9.5.5 on my Macbook Pro 15 (mid 2012) running Catalina 10.15.7 using Retroactive.

When I connect the iPod Nano to the MBP 15 I get this error message:

iTunes cannot read the contents of the iPod “iPod”. Go to the Summary tab in iPod preferences and click Restore to restore this iPod to factory settings.” (SEE IMAGE BELOW.)

IMPORTANT: I hesitate to "restore" the iPod Nano because it DOES CONNECT TO ITUNES and does update, etc. when I connect it to the iTunes that's on a bootable external drive running Mojave.

BOTTOM LINE: Everything works fine running iTunes on Mojave but not Catalina. The difference between iTunes on Mojave and the iTunes on Catalina is that I had to use Retroactive to install iTunes on Catalina.

I have looked all over the place trying to find a solution. Seems to be an obscure issue.

Any suggestions, please?

 

[bogdanw]

From the developer of Retroactive:
"If you connect an Apple device to your Mac, and see "iTunes cannot read the contents of the device. Go to the Summary tab in device preferences and click Restore to restore this device to factory settings":
You may have installed iTunes with Retroactive 1.4 or earlier.
Once you reinstall iTunes using the latest version of Retroactive, iTunes should be able to read the contents of your device as expected.
At the end of the installation process, Retroactive will ask you about iPod syncing. If you need to sync with iPod devices, click "Enable Full Disk Access"."
https://github.com/cormiertyshawn895/Retroactive#syncing-with-a-device

 

[magentawave]

Thank you very much. I assume Restore erases everything on the Nano. Problem is that I had just loaded the Nano with a ton of podcast episodes. Until Big Sur I could open iTunes with the Nano connected and drag podcast episodes from the Nano to my Macbook Pro. Well, that used to be the way iTunes worked but apparently that function was removed with Big Sur. Lame.

I bought an app on the App Store called 'Export for iTunes' for $6 that was supposed to enable me to export selected podcast episodes or playlists from iTunes to my Mac but that app is not working. (Sent developer an email.)

Assuming that app won't do what I need to do, do you have any suggestions for how I can transfer everything that is currently on my 7th gen iPod Nano to my Macbook Pro so that after the Restore I can put it all back on the Nano?

Thanks again!

 

[bogdanw]

I don’t own an iPod Nano. My understanding is that, once you have given Full Disk Access, iTunes will run as expected, no restore needed.
@Grumpus might provide more useful advice
https://forums.macrumors.com/threads/i-found-my-old-ipod.2377868/

 

[Grumpus]

Because of the way it launches iTunes 12.9.5, the Retroactive iTunes installer invites you to give /bin/bash Full Disk Access, and if this access isn't granted then iTunes won't be able to sync your devices. Look at
System Preferences... -> Security & Privacy under the Privacy tab. Scroll down to Full Disk Access and make sure that
there is a checked entry for bash, and if there isn't then use '+' to add /bin/bash to the list.

Finder and iTunes both want to access your iPod when it's plugged in. I suggest ejecting your iPod and exiting iTunes if it's running. Then open a new Finder window and plug in your iPod. When the iPod shows up in the Finder sidebar, click on it and look at the General tab. Make sure that Automatically sync when this iPod is connected is unchecked. Then start iTunes and check to see if you can sync to it. If it doesn't work, reboot and try your iTunes sync again.

In Monterey, the iTunes 12.9.5 syncing problems I've experienced have been due to conflicts with AMPDevicesAgent, which, starting in Catalina, is the background machinery used by Finder to detect and sync iPod and iOS devices. A description of the process can be read in this blog post. Under the heading Stop Finder automatically opening, that post shows a 'defaults write' command to keep Finder from automatically trying to sync your device:

defaults write com.apple.AMPDevicesAgent dontAutomaticallySyncIPods -bool true

This didn't work for me in Monterey, but the blog post was written with Catalina in mind so it may work there. It might not hurt to reboot after doing the 'defaults write' to make sure that no AMPDevicesAgent processes have attached your iPod.

You can also go nuclear to kill the AMPDeviceDiscoveryAgent process at login time via a local launch agent. This is what I do in Monterey.

 

[magentawave]

I finally ran out of the podcast episodes that I had loaded onto my Nano so I restored the Nano in iTunes and now iTunes recognizes the Nano on both of my Macbook Pro's that I used Retroactive to install iTunes.

Thank you!

 

[magentawave]

P.S. Another issue is that iTunes won't let me subscribe to new podcasts. If you feel inclined, please check out this thread: https://forums.macrumors.com/threads/itunes-will-not-let-me-subscribe-to-new-podcasts.2396260/