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I'm not sure this is the right site, but I've spent several hours trying to figure out why I suddenly cannot upload to my Leonardo (actually, a "Pro Micro" with a 32u4) after upgrading to macOS Catalina.

Initially I thought the board was just dead, but I can program it without issues from a Windows machine. I also worked just fine with it a few days ago, before the update to Catalina. Now I'm getting this output:

Arduino: 1.8.10 (Mac OS X), Board: "Arduino Leonardo"

Sketch uses 10226 bytes (35%) of program storage space. Maximum is 28672 bytes.
Global variables use 1000 bytes (39%) of dynamic memory, leaving 1560 bytes for local variables. Maximum is 2560 bytes.

avrdude: ser_recv(): read error: Device not configured
avrdude: butterfly_recv(): programmer is not responding
avrdude: ser_drain(): read error: Device not configured
avrdude: ser_send(): write error: Device not configured
avrdude: ser_recv(): read error: Device not configured
avrdude: butterfly_recv(): programmer is not responding
avrdude: ser_send(): write error: Device not configured
avrdude: ser_recv(): read error: Device not configured
avrdude: butterfly_recv(): programmer is not responding
avrdude: ser_recv(): read error: Device not configured
avrdude: butterfly_recv(): programmer is not responding
avrdude: ser_send(): write error: Device not configured
avrdude: ser_recv(): read error: Device not configured
avrdude: butterfly_recv(): programmer is not responding
Found programmer: Id = ""; type = �
Software Version = .�; Hardware Version = �.�
avrdude: ser_send(): write error: Device not configured
avrdude: ser_recv(): read error: Device not configured
avrdude: butterfly_recv(): programmer is not responding
avrdude: ser_send(): write error: Device not configured
avrdude: ser_recv(): read error: Device not configured
avrdude: butterfly_recv(): programmer is not responding
avrdude: error: buffered memory access not supported. Maybe it isn't
a butterfly/AVR109 but a AVR910 device?
avrdude: initialization failed, rc=-1
     Double check connections and try again, or use -F to override
     this check.

avrdude: ser_send(): write error: Device not configured
avrdude: ser_recv(): read error: Device not configured
avrdude: butterfly_recv(): programmer is not responding
avrdude: error: programmer did not respond to command: leave prog mode
avrdude: ser_send(): write error: Device not configured
avrdude: ser_recv(): read error: Device not configured
avrdude: butterfly_recv(): programmer is not responding
avrdude: error: programmer did not respond to command: exit bootloader
avrdude: ser_close(): can't reset attributes for device: Device not configured
the selected serial port avrdude: ser_close(): can't reset attributes for device: Device not configured
does not exist or your board is not connected

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

My Mega2560 as well as Due work just fine. I even tried re-burning the bootloader into the Pro Micro using the Mega, which worked fine but didn't solve the issue.

I also tried getting into the bootloader mode, by tapping the reset (actually, using a wire to pull RST to GND) button twice. It changes the error to

Found programmer: Id = ">>> SPI"; type = SSoftware Version = >.>; 
Hardware Version = >.
avrdude: error: buffered memory access not supported. 
Maybe it isn't a butterfly/AVR109 but a AVR910 device?
avrdude: initialization failed, rc=-1
Double check connections and try again, or use -F to override this check.

The bootloader trick is not required on Windows, it just works.

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