Model100 won't go into programmable mode

What used to work fine does not anymore:

Model 100 with a working firmware is registered on COM8 on my Windows 10.
Booting to bootloader mode (holding prog while plugging USB (prog lights red)) the Arduino IDE can’t detect the keyboard on any serial port. COM8 is also gone from the machine until I reconnect the keyboard without holding prog.

Using Arduino 1.8.19 with Keyboardio 1.99.8 package

With the keyboard in bootloader mode COM8 disappears from the ports list. I can still see COM1, 5 and 6 (as they have been there the whole time) selecting COM1 lets me upload and the keyboard resets and is on COM8 again with the new firmware.

But the IDE used to be able to find the keyboard in bootloader by itself just fine. Now it can’t. What could be the cause of that?

The model 100 does not use serial for its bootloader mode. when in boot loader mode, I have never seen a serial port show up for it.

Hmm… maybe I’m just remembering wrong.

Speaking of the model 100 bootloader. Will the ‘need to replug usb’ thing ever be fixed?