Thanks for the report.

Are you flashing the board via the ESP-PROG module using a the Enable Programmer option?

There is one more difference between submodules... On DevkitC there is version ESP-WROOM-32D and on DevkitS I put ESP-WROOM-32E (new one recommended for develepment). Maybe debugger dont communicate with 32E version? But I doubt about it...

Dear Simon, thank you so much for your effort. I tried new openOCD yesterday already, but it didnt help. Now I tried again, but there is some problem when openOCD tries to connect to DevkitS module...

New openOCD Log with DevkitS module:

c:\ProgramData\VMicro\tools\openocd-esp32\bin>openocd -d2 -s s/" -f s/interface/ftdi/minimodule-lowcost.cfg" -c "set ESP32_RTOS none" -f s/board/esp-wroom-32.cfg" -c "init; reset halt"
Open On-Chip Debugger  v0.10.0-esp32-20211111 (2021-11-10-21:40)
Licensed under GNU GPL v2
For bug reports, read
        http://openocd.org/doc/doxygen/bugs.html
debug_level: 2

none
Error: libusb_open() failed with LIBUSB_ERROR_NOT_SUPPORTED
Info : clock speed 2000 kHz
Error: JTAG scan chain interrogation failed: all ones
Error: Check JTAG interface, timings, target power, etc.
Error: Trying to use configured scan chain anyway...
Error: esp32.cpu0: IR capture error; saw 0x1f not 0x01
Warn : Bypassing JTAG setup events due to errors
Info : Listening on port 3333 for gdb connections
Error: JTAG scan chain interrogation failed: all ones
Error: Check JTAG interface, timings, target power, etc.
Error: Trying to use configured scan chain anyway...
Error: esp32.cpu0: IR capture error; saw 0x1f not 0x01
Warn : Bypassing JTAG setup events due to errors
Info : esp32: Debug controller was reset.
Info : esp32: Core was reset.
Error: Couldn't halt target before SoC reset
 

New openOCD Log with DevkitC-v4 module:

c:\ProgramData\VMicro\tools\openocd-esp32\bin>openocd -d2 -s s/" -f s/interface/ftdi/minimodule-lowcost.cfg" -c "set ESP32_RTOS none" -f s/board/esp-wroom-32.cfg" -c "init; reset halt"
Open On-Chip Debugger  v0.10.0-esp32-20211111 (2021-11-10-21:40)
Licensed under GNU GPL v2
For bug reports, read
        http://openocd.org/doc/doxygen/bugs.html
debug_level: 2

none
Error: libusb_open() failed with LIBUSB_ERROR_NOT_SUPPORTED
Info : clock speed 2000 kHz
Info : JTAG tap: esp32.cpu0 tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : JTAG tap: esp32.cpu1 tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : esp32: Debug controller was reset.
Info : esp32: Core was reset.
Info : esp32: Detected debug stubs @ 3ffc0820
Info : Listening on port 3333 for gdb connections
Info : JTAG tap: esp32.cpu0 tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : JTAG tap: esp32.cpu1 tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : esp32: Target halted, PC=0x400E8972, debug_reason=00000000
Warn : Not full dbg stub table 1 of 2
Info : esp32: Debug controller was reset.
Info : esp32: Core was reset.
Info : esp32: Target halted, PC=0x500000CF, debug_reason=00000000
Info : esp32: Core was reset.
Info : esp32: Target halted, PC=0x40000400, debug_reason=00000000
Info : Listening on port 6666 for tcl connections
Info : Listening on port 4444 for telnet connections
Info : esp32: Debug controller was reset.
Info : esp32: Core was reset.
Info : esp32: Debug controller was reset.
Info : esp32: Core was reset.
Info : esp32: Detected debug stubs @ 3ffc0820
shutdown command invoked
Info : esp32: Restore debug stubs address 3ffc0820
 

I tried 2 pcs of ESP-Prog, OLIMEX ARM-USB-TINY-H debugger, second computer, cables change, but still there is this problem. It is interesting because DevkitS and DevkitC looks same. If DevkitS module will work properly there is chance to use 16MB Wroom module for developement.

Dear Simon, thank you very much for your advice. It realy helped and the openOCD could be started in background same way as DevkitC module.
Unfortunately there are some new problems with gdb connection.
I tried to combine scripts from openOCD and Visual Micro, set the ESP32 Wrover Module as target but I wasnt successful.
I am getting the error:

Warning:
Cannot insert breakpoint 2.
Cannot access memory at address 0x400d0cdb (ESP32 Wrover Module)
Cannot access memory at address 0x400d0bfe (ESP32 Dev Module) 

Please if possible, check this openOCD log:

Error: libusb_open() failed with LIBUSB_ERROR_NOT_SUPPORTED
Info : clock speed 2000 kHz
Info : JTAG tap: esp32.cpu0 tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : JTAG tap: esp32.cpu1 tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : esp32: Debug controller was reset.
Info : esp32: Core was reset.
Info : esp32: Detected debug stubs @ 3ffc0820
Info : Listening on port 3333 for gdb connections
Info : JTAG tap: esp32.cpu0 tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : JTAG tap: esp32.cpu1 tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : esp32: Target halted, PC=0x400DFA3B, debug_reason=00000000
Warn : Not full dbg stub table 1 of 2
Info : esp32: Debug controller was reset.
Info : esp32: Core was reset.
Info : esp32: Target halted, PC=0x500000CF, debug_reason=00000000
Info : esp32: Core was reset.
Info : esp32: Target halted, PC=0x40000400, debug_reason=00000000
Info : Listening on port 6666 for tcl connections
Info : Listening on port 4444 for telnet connections
Info : accepting 'gdb' connection on tcp/3333
Info : esp32: Target halted, PC=0x40092AEE, debug_reason=00000001
Info : Flash mapping 0: 0x10020 -> 0x3f400020, 45 KB
Info : Flash mapping 1: 0x20018 -> 0x400d0018, 99 KB
Info : esp32: Target halted, PC=0x40092AEE, debug_reason=00000001
Info : Auto-detected flash bank 'esp32.flash' size 16384 KB
Info : Using flash bank 'esp32.flash' size 16384 KB
Info : esp32: Target halted, PC=0x40092AEE, debug_reason=00000001
Info : Flash mapping 0: 0x10020 -> 0x3f400020, 45 KB
Info : Flash mapping 1: 0x20018 -> 0x400d0018, 99 KB
Info : esp32: Target halted, PC=0x40092AEE, debug_reason=00000001
Info : Auto-detected flash bank 'irom' size 16384 KB
Info : Using flash bank 'irom' size 16384 KB
Info : esp32: Target halted, PC=0x40092AEE, debug_reason=00000001
Info : Flash mapping 0: 0x10020 -> 0x3f400020, 45 KB
Info : Flash mapping 1: 0x20018 -> 0x400d0018, 99 KB
Info : esp32: Target halted, PC=0x40092AEE, debug_reason=00000001
Info : Auto-detected flash bank 'drom' size 16384 KB
Info : Using flash bank 'drom' size 16384 KB
Warn : negative reply, retrying
Warn : negative reply, retrying
Warn : acknowledgment received, but no packet pending
Warn : acknowledgment received, but no packet pending
Warn : address 0x400d0bfe not writable
Error: esp32: Failed to write breakpoint instruction (-4)!
Error: esp32: Failed to add SW breakpoint!
Error: can't add breakpoint: unknown reason
Info : dropped 'gdb' connection
 

Some attached logs could help too...
Sorry to take your time, but I hope DevkitS module with 16MB support can be very handy for developers.
Have a nice evening. BR David

The output is from Visual Studio DebugOpenOCD.log). Thank you very much for your new openOCD testing.

Dear Simon, good morning and thank you so much for your support. It will be great to get 16MB ESP32 chips debug working. Yes I used custom json, tried to put the file everywhere, tried to change xml files, use second PC but finaly after few hours found the combobox with Manual/Custom option : ) Anyway it caused good step ahead, I hope the new error (same on both PC) could be fixed.

Unable to start debugging: Failed to find thread 1 for break event 

Micro Build Log

Launching custom debugger: son
Hard resetting via RTS pin...

// MI Debugger Properties
{
  "serverLaunchTimeout": 5000,
  "filterStdout": false,
  "filterStderr": true,
  "targetArchitecture": "arm",
  "stopAtEntry": false,
  "externalConsole": false,
  "MIMode": "gdb",
  "MIDebuggerServerAddress": "localhost:3333",
  "cwd": "C:\\Users\\dak\\AppData\\Local\\Temp\\VMBuilds\\Test002\\esp32_esp32\\Debug",
  "MIDebuggerPath": -elf-gcc\\1.22.0-97-gc752ad5-5.2.0/bin\\xtensa-esp32-elf-gdb.exe",
  "MIDebuggerArgs": "-ex \"set remote hardware-watchpoint-limit 2\" -ex \"mon reset halt\" -ex \"flushregs\" -ex \"thb app_main\" -ex \"c\"",
  "debugServerPath": "C:\\ProgramData\\VMicro\\tools\\openocd-esp32\\bin\\openocd.exe",
  "debugServerArgs": "-d2 -l est002.ino_DebugOpenOCD.log}\" -s \"c:\\ProgramData\\VMicro\\tools\\openocd-esp32/share/openocd/scripts/\" -f ftdi/minimodule-lowcost.cfg\" -c \"set ESP32_RTOS none\" -f 2-wrover-kit-3.3v.cfg\" -c \"init; reset halt\"",
  "setupCommands": [],
  "program": elf",
  "logging": {
    "moduleLoad": false,
    "trace": false,
    "engineLogging": false,
    "programOutput": false,
    "exceptions": false,
    "traceResponse": false
  },
  "visualizerFile": bugger_tmp.natvis",
  "showDisplayString": true
}
 

Debug Log

openocd: Open On-Chip Debugger  v0.10.0-esp32-20211111 (2021-11-10-21:40)
openocd: Licensed under GNU GPL v2
openocd: For bug reports, read
openocd: 	http://openocd.org/doc/doxygen/bugs.html
openocd: debug_level: 2
openocd:
=thread-group-added,id="i1"
GNU gdb (crosstool-NG crosstool-ng-1.22.0-97-gc752ad5d) 7.10
Copyright (C) 2015 Free Software Foundation, Inc.
License GPLv3+: GNU GPL version 3 or later <http://gnu.org/licenses/gpl.html>
This is free software: you are free to change and redistribute it.
There is NO WARRANTY, to the extent permitted by law.  Type "show copying"
and "show warranty" for details.
This GDB was configured as "--host=i686-host_w64-mingw32 --target=xtensa-esp32-elf".
Type "show configuration" for configuration details.
For bug reporting instructions, please see:
<http://www.gnu.org/software/gdb/bugs/>.
Find the GDB manual and other documentation resources online at:
<http://www.gnu.org/software/gdb/documentation/>.
For help, type "help".
Type "apropos word" to search for commands related to "word".
=cmd-param-changed,param="remote hardware-watchpoint-limit",value="2"
Register cache flushed.
Make hw breakpoint pending on future shared library load? (y or [n]) [answered N; input not from terminal]
=cmd-param-changed,param="pagination",value="off"
0x40000400 in ?? ()
[New Thread 1073463852]
[New Thread 1073447000]
[New Thread 1073467960]
[New Thread 1073456088]
[New Thread 1073445228]
[New Thread 1073454676]
=thread-selected,id="1"
[New Thread 1073465264]
Program '' skončil s kódem 42 (0x2a). 

OpenOCD Log

Warn : Interface already configured, ignoring
Error: libusb_open() failed with LIBUSB_ERROR_NOT_SUPPORTED
Info : ftdi: if you experience problems at higher adapter clocks, try the command "ftdi_tdo_sample_edge falling"
Info : clock speed 20000 kHz
Info : JTAG tap: esp32.cpu0 tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : JTAG tap: esp32.cpu1 tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : esp32.cpu0: Debug controller was reset.
Info : esp32.cpu0: Core was reset.
Info : esp32.cpu0: Detected debug stubs @ 3ffc0820
Info : esp32.cpu1: Debug controller was reset.
Info : esp32.cpu1: Core was reset.
Info : Listening on port 3333 for gdb connections
Info : JTAG tap: esp32.cpu0 tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : JTAG tap: esp32.cpu1 tap/device found: 0x120034e5 (mfg: 0x272 (Tensilica), part: 0x2003, ver: 0x1)
Info : esp32.cpu0: Target halted, PC=0x400E8972, debug_reason=00000000
Info : Set GDB target to 'esp32.cpu0'
Info : esp32.cpu1: Target halted, PC=0x400E8972, debug_reason=00000000
Warn : Not full dbg stub table 1 of 2
Info : esp32.cpu0: Debug controller was reset.
Info : esp32.cpu0: Core was reset.
Info : esp32.cpu0: Target halted, PC=0x500000CF, debug_reason=00000000
Info : esp32.cpu0: Core was reset.
Info : esp32.cpu0: Target halted, PC=0x40000400, debug_reason=00000000
Info : esp32.cpu1: Debug controller was reset.
Info : esp32.cpu1: Core was reset.
Info : esp32.cpu1: Target halted, PC=0x40000400, debug_reason=00000000
Info : Listening on port 6666 for tcl connections
Info : Listening on port 4444 for telnet connections
Info : accepting 'gdb' connection on tcp/3333
Warn : No symbols for FreeRTOS!
Info : esp32.cpu0: Target halted, PC=0x40092AEE, debug_reason=00000001
Info : Flash mapping 0: 0x10020 -> 0x3f400020, 45 KB
Info : Flash mapping 1: 0x20018 -> 0x400d0018, 99 KB
Info : esp32.cpu0: Target halted, PC=0x40092AEE, debug_reason=00000001
Info : Auto-detected flash bank 'esp32.cpu0.flash' size 16384 KB
Info : Using flash bank 'esp32.cpu0.flash' size 16384 KB
Info : esp32.cpu0: Target halted, PC=0x40092AEE, debug_reason=00000001
Info : Flash mapping 0: 0x10020 -> 0x3f400020, 45 KB
Info : Flash mapping 1: 0x20018 -> 0x400d0018, 99 KB
Info : Using flash bank 'esp32.cpu0.irom' size 100 KB
Info : esp32.cpu0: Target halted, PC=0x40092AEE, debug_reason=00000001
Info : Flash mapping 0: 0x10020 -> 0x3f400020, 45 KB
Info : Flash mapping 1: 0x20018 -> 0x400d0018, 99 KB
Info : Using flash bank 'esp32.cpu0.drom' size 48 KB
Info : New GDB Connection: 1, Target esp32.cpu0, state: halted 

SW Configuration:
Windows 10 Pro 20H2, build 19042.1348
VS Community 2022 17.0.0, .NET Framework 4.8.04084
Visual Micro 2021.1108.0, Arduino 1.8.16
Zadig 2.7 -> Dual RS232-HS libwdi 6.1.7600.16385
OpenOCD v0.10.0-esp32-20211111
Thank you again for your help & have a nice Tuesday.

Just to update, it is worth trying the latest release (21.11.08-19) available at the top of the board below:
https://www.visualmicro.com/forums/YaBB.pl?board=vs_arduino_ext_releases

To try the latest debugging setup, you will also need to add a local board.txt to the project, with the below entries:

debug.toolingsystem=gdbscript
tools.openocd.debug.path={runtime.tools.openocd-esp32-0.10.1-2021.11.11.path}