I'm hooking up to this thread, because I also have the issue that gdb doesn't work with the ESPPROG interface on my Windows10-machine.

I'm pretty sure, that the WinUSB driver is working correctly, because I'm able to do the upload with vMicro via the ESPPROG interface sucessfully.

But debugger always abort with error code 0xC0000135.

Like you've proposed, I've executed the "openocd.exe" via cmd-shell to see some more information.

I've attached the output of the cmd-shell  and the DebugOpenOCD.log recorded when running the Debug > Attach to Process.

Like suggested I've used the board.txt to set "tools.esp32prog.path".

Just one remark:
After copying your template-path I've had to replace the "/"-char before the "bin" by the "\"-char. Otherwise I did get an error "Unable to start debugging. The value of miDebuggerPath is invalid".

A guy in another thread on another side wrote that the libusb_open() return-message LIBUSB_ERROR_NOT_SUPPORTED was logged for his device as long as the "Logitech receiver" for his weirless keyboard/mouse was attached to another USB port. As soon as he removed the receiver he didn't get that message any more.

Because I'm also using a wireless Logitech keyboard/mouse with this receiver, I've removed this and all other not needed USB-devices from my PC and tried if that could solve the issue. But unfortunately it didn't.
 
Did you have any other ideas to solve the issue?

If not so, the next step for me would be to install the envirement on my second Windows10-PC.

Thanks for your help beforehand

Best regards frk

I've found the solution. Missed your hint about the fault in the ESP core in version 2.0.2.  I've downgraded the ESP32 core to 2.0.1-RC1 and now the Debugger works fine 

So, the issue is solved.

Best regards,
frk