ESP32-D2WD Based Custom board JTAG Flash issue.

[ESP_Sprite]

+1 on upgrading your OpenOCD to a 2020 version. Could be you're using v3 silicon here, that changed some things in the JTAG logic.

[Scott.Bonomi]

Other Forums have reported errors trying to run JTAG with the WROOM that are fixed by getting the
more current version. Unless someone has made a tool change, it is a pain since after removing the installed version and installing the more current release from https://github.com/espressif/openocd-esp32/releases
You will probably have to edit tools.json to reflect the name and hash of the updated version.
I am quite sure I was getting connect failures prior to updating my system. You will want the esp32 specific load of the tool for sure.