Debug Errors Using ESP32 Dev Kit V1 and ESP Prog

Advanced Solutions Debugging
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  1. There were recent bugfixes in the Espressif32 platform regarding a openocd update which fixes many problems that people have experienced, but they are not released as a stable release yet. To still use it, replace platform = espressif32 in your platformio.ini with platform = https://github.com/platformio/platform-espressif32.git and recompile and restart debugging.
  2. the logs show that

JTAG speed is at 20MHz? Your cables can handle that? Better lower the speed in the configuration files as seen in ESP32-Pico-V3 fails to upload/debug using esp-prog - #6 by maxgerhardt (after using the latest platform version).