Krissy has been using her iPod Nano when she exercises for fifteen years at least, I'm vaguely surprised it still holds a charge. The music on it has not been updated since 2010 at least. She does not mind.

"Bring On Defunct: The iPod Enthralls Young Music Listeners"

(gift link)

https://www.nytimes.com/2026/03/01/technology/apple-ipod-music-comeback.html?unlocked_article_code=1.QFA.gq_d.S-ci8J9oWCnc&smid=url-share

Bring On Defunct: The iPod Enthralls Young Music Listeners

It’s not exactly going analog, but people looking to move away from streaming say Apple’s old device is a small step away from constantly being online.

The New York Times
@scalzi
The challenge is adding new music, I tried last summer, for my daughter’s iPod, only to find out that it is asking for an updated iOS in order to link to my computer. I tried with a PC and with a Mac.
It was too old to update new iOS…
@arifell tried an older version mac os vm with an old itunes?
@arifell @scalzi I just tried both my iPod 5th gen and my iPod Touch. They worked no problem with my Mac Mini M4 running Tahoe. Are you just using the Finder interface? Apple Music sees my iPods, but gets a little weird about them.