Bulk transfer playlists to iPod Classic from iTunes on Mac Pro

Ancient technology warning!!!


I've done a restore of my iPod Classic to clear up a mysterious problem, and have manually moved a few playlists from iTunes on 2012 Mac Pro to the iPod. That's worked fine.


Is there a way to do a BULK transfer of my remaining 100ish playlists from my ancient Mac Pro to the iPod Classic? I haven't yet found a trick for that.


There's an inherent challenge moving one by one. When I select a playlist and drag it upward and drop onto the iPod part of the menu, the window automatically scrolls to show the iPod listing. When that happens, I can then drop the current single playlist onto the iPod. Each time, the list of playlists on the Mac Pro gets pushed farther down, so each scroll – in each direction – gets progressively farther. Tedious!!


Is there a trick to this, or is the one-by-one process all that's possible?

I'm motivated enough to proceed one-by-one if I have to, but if there's an alternative, I'll take the easy route.


Thanks for any solutions.

Mac Pro, macOS 10.14

Posted on Jan 10, 2026 8:52 PM

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Bulk transfer playlists to iPod Classic from iTunes on Mac Pro

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