The first part looks like a good debug connection (as e.g. here, up until the Ignoring packet error, continuing……
Related error messages / topics I could find were debugging problem: unrecognized item "timeout" in "qSupported" response - ESP32 Forum and Linux/OpenOCD debugging with ESP-PROG - problem - ESP32 Forum, the latter one again talking about USB power problems.
Problem - can't debug ESP32 wrover under linux - ESP PROG, Jtag · Issue #103 · espressif/openocd-esp32 · GitHub also talks about flash voltage.
…oh. I think I found something?
Go into your C:\Users\<user>\.platformio\packages\tool-openocd-esp32\share\openocd\scripts\board\esp32-wrover.cfg. See the lines
# Tell OpenOCD which SPI flash voltage is used by the board (3.3 or 1.8)
# The TDI pin of ESP32 is also a bootstrap pin that selects the voltage the SPI flash
# chip runs at. When a hard reset happens (e.g. because someone switches the board off
# and on) the ESP32 will use the current TDI value as the bootstrap value because the
# JTAG adapter overrides the pull-up or pull-down resistor that is supposed to do the
# bootstrapping. These lines basically set the idle value of the TDI line to a
# specified value, therefore reducing the chance of a bad bootup due to a bad flash
# voltage greatly.
# This option defaults to 3.3, if not set. To override the default, uncomment
# the following line:
set ESP32_FLASH_VOLTAGE 1.8
now 1.8V for a wrover module seems to be WRONG in the case of your used ESP32-WROVER-IE (datasheet).
I don’t know whether I made the changes for ESP32_FLASH_VOLTAGE locally but, you should maybe check with both options here. Commenting the line use 3.3V flash voltage seems to be the right thing here.