[rnrn]

Do you use some old version of iTunes to put music on it or are there other tools with better support for old iPods?

[neckro23]

Original iPods (and early iPhones) weren’t locked down as much. There were a number of utils that could manage your library. ml_ipod plugin for WinAmp comes to mind.

[liquidise]

All my music gets copied into OS X's Apple Music, which still supports iPods. Other repliees are arguably better alternatives these days.

[echelon_musk]

Rockbox.

[sgerenser]

on macOS you can still manage/sync iPods from the Finder (it was moved to there from iTunes when they killed iTunes).