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Unable to sync iPod Classic in OS Catalina

When I go into finder on OS Catalina, the iPod Classic is in the sidebar. However in the window to the right of the sidebar there are just file folders, no options for sync. How can I make those options appear?

iPod Classic

Posted on Oct 18, 2019 12:02 PM

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Dec 11, 2019 12:55 AM in response to Jhmooney

I resolved syncing an iPod Nano 3rd Generation with a click wheel on Catalina which means that Catalina does support the device and most likely everything released afterwards.


Before I say what I did, try the following: Boot with the iPod plugged in and then immediately open any folder and see if the iPod appears in the sidebar. If so, click on it (the iPod icon that looks like the iPod, not the second icon that looks like a disc or SD Drive) and see if it loads/syncs in the window. After doing what I did, (to be explained below) it would not sync / load for me if I plugged it in after I had booted in Catalina (it would just say loading with a spinning wheel forever) but if I booted in Catalina with the iPod plugged in, and immediately opened a finder folder and clicked on the iPod icon, it would sync and load and allow me to add and remove songs in the finder widows in Catalina. Interestingly enough, if I then ejected it and plugged it right back in again, it would not sync/load, I would just get "Loading" and an infinite spinning wheel. Only rebooting with the iPod connected and going immediately to a folder and clicking on the iPod icon allowed the iPod to sync and then be worked with. So try simply booting in Catalina with the iPod connected at the time of booting and then immediately accessing the iPod thru the Finder as explained above. if it doesn't work, do the following and then try booting in Catalina with it connected:


What I did before simply booting with it connected to Catalina:


I booted under Mojave. I reset the iPod to factory settings. I put my library back on it using iTunes. Then I booted under Catalina with the iPod connected and it worked. If I then ejected the iPod and then pulled the cable out and then plugged the cable back, Finder would show the iPod but it would not sync and load. But if I rebooted with the cable in connected to the iPod, and then immediately opened a window and clicked on the iPod icon, it would sync and load in Catalina. All of this begs the questions, did I ever need to reset and resync under iTunes in Mojave or is getting it to work under Catalina simply a matter of having it connected when it boots and immediately using finder to access the iPod and sync.

Unable to sync iPod Classic in OS Catalina

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