iPod Nano will not sync with iTunes

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I recently bought a secondhand Nano. Though the controls function well, it will not sync with iTunes on my Mac Mini. Any suggestions?
 

chscag

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Your Mac's Specs
2017 27" iMac, 10.5" iPad Pro, iPhone 8, iPhone 11, iPhone 12 Mini, Numerous iPods, Monterey
Which model Nano is it? You can try to do a restore from iTunes and then attempt to sync the music to it again.
 

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