Upload Problems ESP32-S3 TFT Mac OS

Hello - having some problems uploading to ESP32-S3 TFT from Mac Mini - M1 chip, OS Monterey 12.5.1. Was able to build a simple sample program and upload it OK. Since that first upload have not been able to upload anything.
Error: Couldn’t find a board on the selected port. Check that you have the correct port selected. If it is correct, try pressing the board’s reset button after initiating the upload.
*** [upload] Explicit exit, status 1
A little Google searching indicates may be some Mac USB driver issues? Thinking there must be other Mac users that have seen this as well and know the fix?

Update - may not be a USB problem after all. Tried a new ESP32 board and am able to upload programs OK. Thinking it might be a problem with the ESP32. Might have messed up the bootloader?

I have found that when I start working I often need to unplug and replug the USB cable on my Mac Book when the target device port is not found (and then it magically appears). Once it’s found though, it doesn’t disappear.

I’ve tried unplugging and replugging USB, restarting Mac, powering off then on Mac. None of those work. What does seem to work consistently is:
Upload and get error message that PIO couldn’t find board
Double click reset button on ESP32
ESP32 now shows up as a drive in Finder on Mac
Drag Adafruit Factory Reset Program (adafruit-esp32-s3-tft-feather-factory-reset.UF2) to drive in Finder
Original program appears on ESP32
Mac gives “Disk Not Ejected Properly” warning
Am now able to upload program to ESP32 “1” time.

Hey there!

Same problem here, very frustrating. Have you found a solution yet?

Edit: it seems there are some more upload protocols supported, but I couldn’t get any other than esptool to work (but I’m kinda noob). Are you familiar with those? Adafruit Feather ESP32-S3 TFT — PlatformIO v6.1 documentation

Best, P

What m1078 suggested in his post of mar 8 by resetting the device back to the Adafruit factory reset program worked for me. It’s a pia as you have to do this every time you want to upload any new code but it does only take a minute or two to do.