Similar problem here:

Probe Olimex AMT-USB-TINY
VM 1907.14.2

Debug output:
<<<
Starting: "C:\ProgramData\vmicro\tools\openocd-espressif-esp32-10.0.1\bin/openocd.exe" -d2 -s s/" -c "adapter_khz 1000" -f s/interface/ftdi/olimex-jtag-tiny.cfg" -c "set ESP32_RTOS none" -f s/board/esp-wroom-32.cfg" -c "init; reset halt"
Starting: c\1.22.0-80-g6c4433a-5.2.0/bin\xtensa-esp32-elf-gdb.exe" --interpreter=mi
=thread-group-added,id="i1"
~"GNU gdb (crosstool-NG crosstool-ng-1.22.0-80-g6c4433a5) 7.10\n"
~"Copyright (C) 2015 Free Software Foundation, Inc.\n"
~"License GPLv3+: GNU GPL version 3 or later <http://gnu.org/licenses/gpl.html>;\nThis is free software: you are free to change and redistribute it.\nThere is NO WARRANTY, to the extent permitted by law.  Type \"show copying\"\nand \"show warranty\" for details.\n"
~"This GDB was configured as \"--host=i686-host_pc-mingw32 --target=xtensa-esp32-elf\".\nType \"show configuration\" for configuration details."
~"\nFor bug reporting instructions, please see:\n"
~"<http://www.gnu.org/software/gdb/bugs/>.\n"
~"Find the GDB manual and other documentation resources online at:\n<http://www.gnu.org/software/gdb/documentation/>.\n"
~"For help, type \"help\".\n"
~"Type \"apropos word\" to search for commands related to \"word\".\n"
(gdb)
"C:\ProgramData\vmicro\tools\openocd-espressif-esp32-10.0.1\bin/openocd.exe" exited with code 1 (0x1).
>>>

Zadig Driver done --> see attachement

Is there an other info, log files, ... I can provide to fix the issue?

Any help is appreciated
Regards

The debuggers have been refreshed and tested in 1907.15. It should produce better results. Please try. If it fails please post the requested info so we can see your config + post the debugger output again but hopefully it works for you now.

Thanks for all the info

Please paste the following into a cmd prompt and press enter. What do you see if anything?

"C:\ProgramData\vmicro\tools\openocd-espressif-esp32-10.0.1\bin/openocd.exe" -d2 -s s/" -c "adapter_khz 1000" -f s/interface/ftdi/olimex-jtag-tiny.cfg" -c "set ESP32_RTOS none" -f s/board/esp-wroom-32.cfg" -c "init; reset halt" 

Error window from above point 3 --> gdb_error4.PNG

Thanks that's useful we will find the solution over the next day or so.

By the way the compile/upload doesn't affect things other than to have made one upload with correct optimization setting and a generic hardware debug flag. After that you can click "Debug>Attach To Process" which attempts to start the debugger (or attempt to start it) using which hardware debugger is currently selected.

more to follow

To change this in the interim you can add a Local Boards.txt to your Project (right click project in solution explorer, Add menu > Add Local Boards.txt)

Then add the below line of text to it and save:

fg
 

Click save on the board.txt to be sure it has sabed.

Then ensure you still have the "Olimex ARM-USB-TINY" Debugger selected, and try to attach again, it should hopefully find the correct device now and connect.... (might need to build first)

Could you paste and run the following in a command prompt and send back all of the output (this has the amended cfg file present as you spotted previously, to match your debugger hardware), hopefully it will reveal more information:

"C:\ProgramData\vmicro\tools\openocd-espressif-esp32-10.0.1\bin/openocd.exe" -d2 -s s/" -c "adapter_khz 1000" -f s/interface/ftdi/olimex-arm-usb-tiny-h.cfg" -c "set ESP32_RTOS none" -f s/board/esp-wroom-32.cfg" -c "init; reset halt"  

Thanks Roger, and I hadn't spotted that this was all already done.

Would you be able to try the below command? 
(this is manually configuring the Olimex as the manufacturer did in the previous release, both old and new configurations work on my Olimex-Arm-Usb-Tiny with ESP32 and its relevant details)

"C:\ProgramData\vmicro\tools\openocd-espressif-esp32-10.0.1\bin/openocd.exe" -d2 -s s/" -c "adapter_khz 1000" -c "echo {***** Manual OCD-CFG ****}" -c "interface ftdi" -c "ftdi_device_desc {Olimex OpenOCD JTAG ARM-USB-TINY-H}" -c "ftdi_vid_pid 0x15ba 0x002a" -c "ftdi_layout_init 0x0808 0x0a1b" -c "ftdi_layout_signal nSRST -oe 0x0200" -c "ftdi_layout_signal nTRST -data 0x0100 -oe 0x0100" -c "ftdi_layout_signal LED -data 0x0800" -c "echo {***** BOARD CFG *****}" -c "set ESP32_RTOS none" -f s/board/esp-wroom-32.cfg" -c "init" -c "echo {***** RUNNING ****}" -c "sleep 1" -c "shutdown"
 

Hopefully this will show something additional, and thanks again for all the detail.

Thanks Roger, and as you say it feels like it must be a connection at present... 

If you disconnect the ESP32 and ribbon from the olimex, and run the same command, you should see some further messages similar to the below, beyond what we have seen so far... (just helps confirm the debugger is connecting as expected)

Info : clock speed 2000 kHz
Error: JTAG scan chain interrogation failed: all ones
Error: Check JTAG interface, timings, target power, etc.

After that it feels like its either the wiring, or the target board itself.   

Can you confirm:-
1) which of the many ESP32 Dev modules it is (on the back normally)
2) how it is connected to the Olimex (just pin to pin wiring from Olimex to ESP, or using ribbon/adapter/breakouts)

Our Wiring - https://www.visualmicro.com/page/ESP32-Debugging.aspx

The connector shown is essentially the male Olimex connector, not the female end of a ribbon cable

Today I've got the FT2232H Dual RS232 in the mail. Tried it and it works like a charm! Still don't know why the Olimex doesn't work...