How do I move tracks /files off my 20 year old ipod nano onto my new MacBook Air?

I have a new MacBook Air and an ~20 year old ipod nano (5th generation). I can't get them to talk to each other. I can get the ipod into disc mode but the new Mac won't read it. For that matter, it isn't working with a a 13 year old Mac, either. I'd like to get the music uploaded somewhere, somehow. Any suggestions?

MacBook Air 15″

Posted on Jan 4, 2026 11:10 AM

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Posted on Jan 4, 2026 2:34 PM

iMazing can transfer music from your iPod nano to your Mac. There is a free trial (see the iMazing FAQ, as there are some limitations in the free trial) so you can see if it does what you want before purchasing.


I have used iMazing for a number of years & versions. It works well and in my case has actually saved me from a Mac calendar sync failure.

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Jan 4, 2026 2:34 PM in response to TBMorris

iMazing can transfer music from your iPod nano to your Mac. There is a free trial (see the iMazing FAQ, as there are some limitations in the free trial) so you can see if it does what you want before purchasing.


I have used iMazing for a number of years & versions. It works well and in my case has actually saved me from a Mac calendar sync failure.

Jan 4, 2026 1:01 PM in response to TBMorris

The system was never designed to do what you want it to do.


Copying music between a computer and an iPod nano was always one-way: from a Mac or a Windows PC, to an iPod nano. You could only synchronize an iPod nano against one computer at a time: if you synchronized it with another computer or library, that wiped all of the music loaded previously.


In addition, the iPod did not store the music out "in the open" where you could copy it off by treating the iPod as a USB flash drive. The idea was that you safeguarded the iTunes library (now the Music library) on your Mac (or PC) by making and keeping backups of it. If you got a new iPod (either because you upgraded, or because something bad happened to the old one), you would load it from the library that you were keeping safe on your computer.


There may have been technical reasons behind some of this, but it is likely that this was also a sop to the recording industry.

How do I move tracks /files off my 20 year old ipod nano onto my new MacBook Air?

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