Problems using Arduino IDE debugger

Official Hardware Nano Family Nano ESP32
1

Continuing the discussion from Debugging on the new Nano ESP32:

Hello,

I am trying to start debugging with my Nano ESP32 board.

I have tried method1 and I get this error:
Sketch uses 254633 bytes (8%) of program storage space. Maximum is 3145728 bytes.
Global variables use 18824 bytes (5%) of dynamic memory, leaving 308856 bytes for local variables. Maximum is 327680 bytes.
esptool.py v4.5.1
Serial port COM3
Connecting......................................

A fatal error occurred: Failed to connect to ESP32-S3: No serial data received.
For troubleshooting steps visit: https://docs.espressif.com/projects/esptool/en/latest/troubleshooting.html
Failed programming: uploading error: exit status 2

With method 2 I don't see the debug button enabled (it says no board selected).

Not sure what else to try.

2

Somehow when I opened the Blink sketch it enabled the debugging mode but now I get this error:

Waiting for gdb server to start...[2023-12-17T23:21:49.759Z] SERVER CONSOLE DEBUG: onBackendConnect: gdb-server session connected. You can switch to "DEBUG CONSOLE" to see GDB interactions.
"C:\Users\nfi\AppData\Local\Arduino15\packages\esp32\tools\openocd-esp32\v0.11.0-esp32-20221026/bin/openocd" -c "gdb_port 50000" -c "tcl_port 50001" -c "telnet_port 50002" -s "c:\Users\nfi\Documents\Arduino\MyBlink" -f "C:/Users/nfi/AppData/Local/Programs/Arduino IDE/resources/app/plugins/cortex-debug/extension/support/openocd-helpers.tcl" -f debug.cfg
Open On-Chip Debugger v0.11.0-esp32-20221026 (2022-10-26-14:48)
Licensed under GNU GPL v2
For bug reports, read
http://openocd.org/doc/doxygen/bugs.html
CDRTOSConfigure
Info : only one transport option; autoselect 'jtag'
Info : esp_usb_jtag: VID set to 0x303a and PID to 0x1001
Info : esp_usb_jtag: capabilities descriptor set to 0x2000
Warn : Transport "jtag" was already selected
Info : Listening on port 50001 for tcl connections
Info : Listening on port 50002 for telnet connections
Error: esp_usb_jtag: could not find or open device!

[2023-12-17T23:21:50.888Z] SERVER CONSOLE DEBUG: onBackendConnect: gdb-server session closed
GDB server session ended. This terminal will be reused, waiting for next session to start...