ipod shuffle 2nd gen question

Joined
Mar 15, 2006
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Your Mac's Specs
2015 Retina 4K iMac. Monterey. 8GB RAM. Crucial 500GB external SSD
I seem to recall that while the ipod is connected to the mac via the charger, I could double click a song and it would play in itunes.

now it dont. how come?

am I missing something? how do I get it to do this again?
 

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