Troubleshooting ESP32 "A fatal error occurred: Failed to connect to ESP32: Timed out waiting for packet header"

Illustration 1: ESP32 connect error

If you plugged in your USB cable into ESP32 and tried to start upload your sketch and this error message appears: "A fatal error occurred: Failed to connect to ESP32: Timed out waiting for packet header" then I think you are frustrated because you searched a lot for a solution and you don't find one. So it was by me, I know this feeling, I searched in the internet and wasted a lot of time to find a solution but unfortunately I do not found a 100% complete solution for this problem.

So I started analyzing the board. After a lot of time I found a working solution for me.

This solution is tested with a MacBook running MAC OSX. I think this will works with Windows and Linux, too. Write down in comments below if you tested it with an other OS.

Troubleshooting 

Configure

First of all you have to configure your Arduino IDE for ESP32 correctly. I described it here.

Serial communication

Optional download and install python serial communication via commandline

sudo pip install pyserial 

Upload

Illustration 2: ESP32 from top

Now be carefully. Before connecting your ESP32 to computer, press and hold the EN button and then connect your ESP32 to computer and start uploading your code. If "Connecting" message in console appears, release EN button and press and hold BOOT button. Now the IDE upload your code on ESP32 board.