I recently setup an ESP32 Dev Kit and ESP-prog to test hardware debugging with VisualMicro. 

I installed the USB drivers and two COM ports are visible. (Related question: which one do I use in Visual Micro?)

Looks good up to this point. However, when I try to initiate a debug session using the >START button, the initial upload fails with the messages pasted after this post. 

I have set ESP32 PROG as the programmer. 

I have also included screen shots of: 

- Visual Studio screen shot showing output at time of failure
- Visual Micro debug config 
- COM port configuration showing driver info


----- output of vMicro upload attempt ---

Debugger: ESP32 PROG
Compiling 'ESP-Prog Debug Test' for 'ESP32 Dev Module                                                                                                              (esp32_esp32)'
Program size: 246,529 bytes (used 13% of a 1,966,080 byte maximum) (13.71 secs)
Minimum Memory Usage: 16376 bytes (5% of a 327680 byte maximum)
 
Uploading 'ESP-Prog Debug Test' to 'ESP32 Dev Module                                                                                                              (esp32_esp32)' using 'ESP32 PROG'
Uploader started for board ESP32 Dev Module                                                                                                              (esp32_esp32)
Uploader will use programmer name: esp32prog
C:\ProgramData\vmicro\tools\openocd-espressif-esp32-10.0.1\bin\openocd.exe -d2 -s s/" -f "interface/ftdi/minimodule-lowcost.cfg" -f "board/esp-wroom-32.cfg" -c "echo -n {****[vMicro]**** Uploading App :}" -c "telnet_port disabled; program s/partitions/boot_app0.bin} 0xe000" -c "echo -n {****[vMicro]**** Uploading Bootloader :}" -c "program {C:\Users\admin\AppData\Local\Temp\VMBuilds\ESP-Prog Debug Test\esp32_esp32\Debug/ESP-Prog Debug Test.ino.bootloader.bin} 0x1000" -c "echo -n {****[vMicro]**** Uploading Sketch :}" -c "program {C:\Users\admin\AppData\Local\Temp\VMBuilds\ESP-Prog Debug Test\esp32_esp32\Debug/ESP-Prog Debug Test.ino.bin} 0x10000" -c "echo -n {****[vMicro]**** Uploading Partitions :}" -c "program {C:\Users\admin\AppData\Local\Temp\VMBuilds\ESP-Prog Debug Test\esp32_esp32\Debug/ESP-Prog Debug Test.ino.partitions.bin} 0x8000 reset; shutdown"
Open On-Chip Debugger  v0.10.0-esp32-20190313 (2019-03-13-09:57)
Licensed under GNU GPL v2
For bug reports, read
     http://openocd.org/doc/doxygen/bugs.html
debug_level: 2
adapter speed: 2000 kHz
Info : Configured 2 cores
esp32 interrupt mask on
****[vMicro]**** Uploading App :Error: libusb_open() failed with LIBUSB_ERROR_NOT_FOUND
Error during upload using programmer
The uploader process failed

The uploader process failed
The uploader returned an error
Error: no device found
Error: unable to open ftdi device with vid 0403, pid 6010, description 'Dual RS232-HS', serial '*' at bus location '*'
** OpenOCD init failed **
shutdown command invoked
Warn : Flash driver of esp32.flash does not support free_driver_priv()
Warn : Flash driver of irom does not support free_driver_priv()
Warn : Flash driver of drom does not support free_driver_priv()

Thanks for the report.

You will need to install the WinUSB Driver using the Zadig tool on Interface 0 of the ESP-PROG for Visual Micro to be able to connect to it:
https://www.visualmicro.com/page/Zadig-Driver-Installation-Guide.aspx

There is a YouTube Video for the ESP-PROG which goes through this process and other details about the ESP-PROG probe:
https://www.youtube.com/watch?v=d6toH-qJbOI

Also note your project and INO files have spaces in the name which often results in issues, and is not compatible with the Arduino Specifications, so it is best to recreate this without the spaces in the names to reduce the potential for problems.

Reinstalled WinUSB driver via ZaDig (ZaDig already showed it as installed). No change. 

Rebooted and environment is now working!

The reboot was apparently the key. 

Thanks!