Hi Luca,
Thanks for your response.
The difference between the upload button and the upload using programmer menu is now clear to me!
The board that i reported as being identified as "ESP32S3 Dev Module" is now back to normal by using the B1+GND (method 1).
Ok, with the board being "ok", i will start from scratch to give you a clear idea of the steps i take:
*I am using a linux box (linux mint 20.3 cinnamon). I have downloaded ver. 2.2.1 (precompiled) and running ./arduino-ide to start the ide. At this point the board is NOT connected to the USB port.
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I start the ide (by running ./arduino-ide in the related folder).
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I click on menu File->New sketch and a new IDE window opens up. I close the old one and keep the one with the new sketch. In the board selector drop down control i can only see "Arduino Nano ESP32" & port /dev/ttyS0. The debug button IS enabled. I save the sketch with a name "new01".
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I connect the board to the USB port. I almost instantly see the board selector drop down control showing 3 options: 1) The one i already mentioned above, 2) "Arduino Nano ESP32" & port /dev/ttyACM0 and 3) "Arduino Nano ESP32" 1-7. *The third option appeared after i added a udev rule for the board to function. After connecting the USB port, the board selector drop down control automatically shows in bold option 2. All Options work for uploading the code to the board. At this point i have not tried pressing the debug button yet.
*The menu Tools->Get board info returns:
BN: Arduino Nano ESP32
VID: 0x2341
PID: 0x0070
SN: 3485187AA59C (w/o semicolons)
- I follow the guide in the page "Debugging with the Nano ESP32". I select menu Tools->USB mode->Debug mode (Hardware CDC), menu Tools->Programmer->Esptool (was already selected), menu Sketch->Optimize for debugging.
5.0) Apply Method 1: Short B1 to GND & keep shorted & confirm the RGB goaes constant green, press & release the RST button and confirm that the RGB goes purle, remove the short between B1 & GND. Now,
5.1) I confirm that the board selector drop down control now shows 2 options: 1) "Arduino Nano ESP32" & port /dev/ttyS0, 2) "WiFiduinoV2" & port /dev/ttyACM0 and none of the two is in bold.
5.2) I manually select the board by using the "Select other board and port" from the board selector drop down control. Board selected: "Arduino Nano ESP32" & port /dev/ttyACM0 Serial Port (USB).
5.3) Upload the empty sketch to the board by selecting menu Sketch->Upload Using Programmer instead of the upload button!!! The upload process is completed successfully.
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I manually reset the board by pressing/releasing the RESET button on the board. Nothing changes in the board selector drop down control.
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I confirm that the Tools menu shows: "Board: Arduino Nano ESP32", "Port: /dev/ttyACM0". Selecting menu Tools->Get board info shows a dialog with the following:
BN: WiFiduinoV2
VID: 0x303a
PID: 0x1001
SN: 34:85:18:7A:A5:9C
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I confirm that at this point there is a file (new tab in the IDE) named: "debug_custom.json". I delete that from the file system. No changes are observed in the board selector drop down control.
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I press the debug button and i get an error:

If not mistaken, this thread suggests the issue remains unresolved.
*They are right discussing the fact that ESP32-S3 is not ARM and also that a risk-V gdb exec is there.
I have only installed the Arduino DebugUtils (by Arduino) so far. There are a few debuggers in the library manager. Should i install any of them?
Regards
Manos