Mac: Sees tty.usbmodem1441 for Circuit Playground, not Feather 32u4

I'm having trouble connecting to my Adafruit Feature 32u4 from my Mac (actually, also from my Windows machine, but leave that for another time...)

I can plug in my Circuit Playground with the same cable and it shows up instantly at /dev/tty.usbmodem1441 and I can upload a sketch and everything is wonderful. When I unplug it and switch in the Feather, the LED on the Feather lights up but I don't get a port.

Any thoughts?