Cannot use Model01 on mac osx lock screen (continues on 10.14.2)

I had to start over with a new fork, evidently the code I was using was far outdated.

I’m all setup with a new fork of the keyboardio/Model01-Firmware and I cannot get the firmware uploaded. Similar to Normal flashing won't work, port lost and keyboard crashed, I get no Prog light when plugging in, though I can see the keyboard type change in the system preferences.

My old layout is still working (typing on it now), but I cannot connect to port to upload. I have rebooted just to be sure. Unplugging/replugging doesn’t light up Prog, but unplugging/press Prog/replugging will light it up, but I still get the dreaded error message.

Arduino: 1.8.5 (Mac OS X), Board: "Keyboardio Model 01"

WARNING: Category 'Debug' in library Kaleidoscope-Hardware-Virtual is not valid. Setting to 'Uncategorized'
Sketch uses 24770 bytes (86%) of program storage space. Maximum is 28672 bytes.
Global variables use 1407 bytes (54%) of dynamic memory, leaving 1153 bytes for local variables. Maximum is 2560 bytes.
Couldn't find a Board on the selected port. Check that you have the correct port selected.  If it is correct, try pressing the board's reset button after initiating the upload.

This report would have more information with
"Show verbose output during compilation"
option enabled in File -> Preferences.

What am I missing here - clearly the board is plugged in and operating normally with old firmware.