Arduino IDE often gets confused when more than one Arudion is connected to a PC

Yes, there are both BOOT and RESET buttons.

A new Feather has arrived. Tried it on Windows 11 PC. Let's say it uploaded fine for about 7 times and then failed with:

Port monitor error: command 'open' failed. Serial port not found. Could not connect to COM32 serial port.

at the bottom right. In the Serial Monitor, it states:

A serial exception error occurred: Cannot configure port, something went wrong. Original message: PermissionError(13, 'A device attached to the system is not functioning.', None, 31)
Note: This error originates from pySerial. It is likely not a problem with esptool, but with the hardware connection or drivers.

For troubleshooting steps visit: Troubleshooting - ESP32 - — esptool latest documentation
Failed uploading: uploading error: exit status 1

I noticed that Under Tools->Port, the board is listed as "COM31 (ESP32 Family Device)".

When it worked, it was listed as"Adafruit Feather ESP32-S3 2MB PSARM" which is listed under Board.

Just pressed the Reset button on the board and 'COM32 Adafruit Feather ESP32-S3 2MB PSARM" showed up under Port. However, during upload, the same set of errors mentioned in post#62 showed up again. Then, under Tools->Port, it changed back to "COM31 (ESP32 Family Device)".

Pressed the Reset button again and this time upload worked. Under Tools->Port, it is identified as "'COM32 Adafruit Feather ESP32-S3 2MB PSARM".

So it seems to be that during upload whenever the port lists "ESP32 Family Device", uploading fails. Whenever it lists "'COM32 Adafruit Feather ESP32-S3 2MB PSARM", it works.

All the time today, I use an usb cable with one end of the big connector and the other end usb-c.

As I understand it, you get the same failure with multiple boards and multiple cables. That means your PC has a problem. Have you ever inserted a USB stick that was in another PC at some point?

But the Mac also has the same problem both with the Feather we tried last week and the new Feather.

There have been several USB sticks at the back of the Windows 11 PC. No insert of any other new USB stick to the PC except for the new Feather.

My feeling is that there is something wrong with this Feather ESP32 S3 product. Sometimes they work but somtimes they suddenly decide to fail. Cannot identifiy specifiic condition(s) that they fail. Can any other Feather ESP32-S3 users confirm this?