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

I don't know, but I do if I don't see any output on my Serial monitor. It can not hurt anything.

Totally normal, assuming your board is already selected then everything is normal and will work. Does it work or not. ONLY for the Mac.

Did you click the port? If so that is why there is a checkmark. If you didn't click, it's the Mac being smart and figuring it out for itself. That doesn't always work and is not a flaw for us to figure out, Just select the one and only port and you are ready. I don;t recall if windows works that way, but don;t care for now.

With the "Select Other Board and Port" window opened, I can see that whenever I press the Reset button on the Feather, "/dev/cu.usbmodem3101 Serial Port (USB)" with a check mark disappeared briefly and then showed up automatically again. Tried over 10 times and that "Port monitor error" which showed up often about 10-15 minutes ago doesn't show up.

To avoid possible stability issue, shall I go ahead and order the Satechi cable you mentioned? Does the length matter?

I did not click the port.

Now that "Port monitor error" showed up again. However, the "Select Other Board and Port" window still shows the same thing as Post#41. Very strange. I thought the one with a check mark would have disappeared when that "Port monitor error" showed up.

Sorry, too many words, pictures are better, but I am pretty sure that the cable is bad. If you can use another cable (I have several dozen, doesn't everyone?)
Let me know if you have another cable; if you do, we will continue; if you don't, I can't help you.

I have never seen that error.

Here is the AI summary. BTW, do you have a Brail driver on your Mac?

A "Port monitor error" on Mac with Arduino IDE usually means a driver issue (especially CH340), a bad USB cable (charging-only), software conflict (like BRLTTY), or a glitch, fixed by reinstalling drivers, using a data USB cable, checking System Information for the port, or even a simple reboot or different port.

Here are the nitty gritty details.

Common Causes & Solutions:

  1. USB Cable Issues:
  • Problem: Using a "charging-only" USB cable that lacks data wires.
  • Solution: Use a known good data cable, try a different USB port on your Mac, or ensure LEDs light up on the board (indicating power/data).
  1. Driver Problems (CH340/FTDI):
  • Problem: Your Mac lacks or has a corrupted USB-to-Serial driver (common with WCH CH340 chips).
  • Solution:
    • Check System Information: Go to Apple Menu > About This Mac > System Report > USB to see if the device is listed.
    • Reinstall Drivers: Uninstall any existing drivers and reinstall the latest official ones (e.g., from Silicon Labs or WCH).
  1. Software Conflicts (BRLTTY):
  • Problem: Background processes like BRLTTY can grab the serial port.
  • Solution: Disconnect the Arduino, open Terminal, run dmesg -w, then reconnect the Arduino to see if BRLTTY appears in the output and uninstall it if it does.
  1. Port Glitch / Sketch Issue:
  • Problem: The IDE or board gets into a bad state.
  • Solution:
    • Restart: Close and reopen the Arduino IDE, or reboot your Mac.
    • Test Sketch: Upload a simple BareMinimum sketch to rule out code interference.
  1. Permissions/Access:
  • Problem: macOS security settings or file permissions.
  • Solution: Ensure the Arduino IDE has necessary permissions in System Settings > Privacy & Security.

Quick Fix Checklist:

  1. Check Cable/Port: Use a data cable and different USB port.
  2. Reboot: Restart Mac and IDE.
  3. Check System Info: Verify device recognition.
  4. Update/Reinstall Drivers: For CH340/FTDI chips.
  5. Check Terminal: Use ls /dev/cu.* to see available ports.

Check out this previous forum post HERE

And do a google search like as follows. That should keep you busy for a few days, I will be AFK for a while.

Good luck.

I don't think I have Brail driver installed on my Mac. Of course I got lots of cables. If that Satechi one works stabily for your Silicon Mac, I might perhaps just get the same.

First try some of your existing USB-C to USB-C. If any are any good the Mac hooks up almost instantly.

I don;t have that specific one, my last cable was this

I found the Satechi by using the filters, either will work.

BTW, I just tossed an Anker cable in the garbage because it was also intermittent like yours. I will never buy another Anker cable, or even a power bank as I had an expensive Anher that swelled up.

I have been an Anker customer for so long that I don't even remember when I started using their products which used to be very good. What happened to this company? Drop in QC?

Me too.

Have you tried a different cable? AFAIK this issue is solved.

Currently I am testing an USB Type C to USB 3.0 Adapter with that cable with old USB connector at one end and new connector at the other. I may try other cables later. I will report back later today or tomorrow.

If you change too many things, it makes it more difficult. I am solely focused on the Mini connected to the feather with a USB-C cable.
As soon as a different cable works, this topic needs to be closed. Mark post 49 as the solution.

Tried OWC TB5 and that expensive Apple's TB4 cables. Both failed. Here is a screenshot of the one with Apple's TB4 cable. Is Arduino IDE or Feather ESP32-S3 being picky? Shall I also avoid using cables with a thunderbolt symbol on it?

Closed the Arduino IDE and re-launched it again. Then, the Apple's TB4 cable works. Something strange is going on.

It's the feather. You can follow the instructions on screen, but I would just toss the card.

Why would you not use Thunderbolt cables? They are the highest grade.

Just order a new feather.

I am moving on.

Is there a BOOT button as well as a RESET? If so, try holding down the BOOT button before you see the 'Connecting' message. You can hold it from the start, it won't hurt anything.
Since it did work at least once without that I doubt it is the solution, but it's worth a try.

The reality is this. A TB4 cable worked at least once but it failed before and I have no doubt it will fail again. That means either a second cable has a loose connection or the problem is in the feather. Have you tried a Win PC again? Remember you may have to try several times, but what we are looking for is a single success because that means it is not an OS issue. Since you changed cables, it is not a cable issue. That leaves only the feather. I would be looking at keeping the feather from moving while trying at least 5 times. If all are ok OR all are failures, then I would intentionally move the feather constantly while the upload is underway. If it is the feather, it will likely fail all 5 times.

Personally, my time is more valuable than a board; just order another.