downhomechunk,
@downhomechunk@midwest.social avatar

I totally get that! Everyone here is suggesting complicated virtualization options. Maybe they know something I don’t. But if it were me, I’d try setting up plain old WINE and seeing if I can install an old version of iTunes from here:

www.oldversion.com/windows/itunes/

You could pick an xp era iTunes and set wine compatibility to xp, or 7 or whatever was contemporary for the ipod generation you have.

Unrelated: my phone insists on autocorrecting ipod to iPad. I feel old now.

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