Audioquest Dragonfly Red

Will Dragonfly red work with iPhone or iPad Pro camera adapter headphone cable plugged to high end computer 
speakers with subwoofer?
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Yep!  You’ll want a USB 3 camera adaptor cable as the other USB camera cable has issues with audible popping noises.  

A jitterbug improves the sound of the Dragonfly and you should consider one as well.  It’s a power conditioner / jittrr reducer and it just smooths out the sound and makes the Dragonfy sound really nice.

What are the speakers that you are trying to connect it to?