It's great that you were able to check at least. So the headphone cable you have has 4 wires? GND, left, right, and mic?
Hmm, do you have different resistor values? Maybe you could try removing the Pico for now and just adding a low value (around 75 Ohm?) resistor between GND and the mic wire? It might be the Mac is looking for a more hefty resistance across the line?
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