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I have an 6th generation iPod Classic (model MC297LL). Current versions of iTunes no longer support this device, so I'm using an older Mac to sync my music, using iTunes 10.5.2. My primary machine is a 2015 "Core i7" MacBook Pro (model MacBookPro11,4).

To avoid having to keep a decade+ old desktop computer set up in my house, I was hoping there might be an OS version compatible with my MacBook Pro that I could install that had a still-compatible version of iTunes. Specifically, I plan to install it as a bootable partition on an external drive.

According to this OS compatibility chart, the oldest version of the OS that can be run on my laptop is OS X Yosemite 10.10.3. I've installed OS 10.10.5 using the installer proved by Apple in its How to get old versions of macOS documentation. This comes included with iTunes 12.2.1.16. However, I do not see my iPod Classic show up when I connect it, which leads me to suspect this version of iTunes is too new.

Before I spend even more time tracking down and installing version 10.10.3 of OS X and/or an older version of iTunes compatible with Yosemite, I would like to know whether this is even doable on this machine. The History of iTunes Wikipedia article makes no mention of when support for the iPod Classic was dropped from iTunes, and I have not had luck finding this information in a web search.

What version of iTunes dropped support for syncing music with the iPod Classic? What is the latest version of iTunes that supports it, and the latest version of the Macintosh operating system that it can be run on?

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  • Confirmed it works in Mojave with iTunes 12.9.55 Not certain of iPod generation, but running iOS 1.3 30GB version, possibly was the iPod Photo judging by the Apple identifier - support.apple.com/HT204217
    – Tetsujin
    Commented Jan 31, 2021 at 11:17

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iPod classic continues to be supported when device syncing was moved from iTunes into the Finder. No device support was removed from iTunes.

If you're having trouble synchronising an iPod with a newer Mac, that sounds like a specific issue that would warrant a specific question.

I can't find the Twitter thread I saw on this topic, but I've found this video that also demonstrates it: https://www.youtube.com/watch?v=fV3itfJyyMM.

An Apple Support article for Big Sur also mentions syncing of iPod classic/nano/shuffle: https://support.apple.com/en-gb/guide/mac-help/mchl923c1147/mac

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