I have tried using both the Arduino IDE and the CLI however I can not get the sketch to upload to the board. The CLI seems faster/easier but the Pro Micro only lasts ~8 seconds in the bootloader mode before it leaves which is just not enough time.
Sketch uses 3460 bytes (12%) of program storage space. Maximum is 28672 bytes.
Global variables use 149 bytes (5%) of dynamic memory, leaving 2411 bytes for local variables. Maximum is 2560 bytes.
Performing 1200-bps touch reset on serial port COM5
Waiting for upload port...
No upload port found, using COM5 as fallback
"C:\Users\User\AppData\Local\Arduino15\packages\arduino\tools\avrdude\6.3.0-arduino17/bin/avrdude" "-CC:\Users\User\Documents\Arduino\hardware\sparkfun\avr/avrdude.conf" -v -patmega32u4 -cavr109 -PCOM5 -b57600 -D "-Uflash:w:C:\Users\User\AppData\Local\Temp\arduino\sketch-CE596C25A0450F1F79A89C6F70DAEE26/Empty.ino.hex:i"
avrdude: Version 6.3-20190619
Copyright (c) 2000-2005 Brian Dean, http://www.bdmicro.com/
Copyright (c) 2007-2014 Joerg Wunsch
System wide configuration file is "C:\Users\User\Documents\Arduino\hardware\sparkfun\avr/avrdude.conf"
Using Port : COM5
Using Programmer : avr109
Overriding Baud Rate : 57600
avrdude: ser_open(): can't open device "\\.\COM5": The system cannot find the file specified.
avrdude done. Thank you.
Error during Upload: Failed uploading: uploading error: exit status 1
Ah. What I found is that when you run the below, if you run the script first and then wait for the upload line to appear you can double press the reset button right when that shows up and then there is no “timing it” since the script is waiting for the board.