After updating VisualGDB to 6.0r3 everything works fine with debugging. I use the ESP Prog for debugging. But for Arduino projects debugging is not possible. Before updating to 6.0r3 also Arduino projects debugging worked without any problems.
Now, if I use the JTAG for flash and debug I get a flash error. See attachment. If I use the Arduino tolls for flashing I get a GDB Session Error.
It looks like an issue between OpenOCD and a particular board. We do not know what is causing it – both the ESP32 OpenOCD port and the board are provided by Espressif.
Our best advice would be to first get it working via command line (i.e. being able to program FLASH on the same board with OpenOCD manually). When this works, we can help you configure VisualGDB to match the OpenOCD command line that worked.