ESP32 button push for programming... on some computers

Hi all, I am using a ESP32-DEVKITC-VE https://www.digikey.ca/en/products/detail/espressif-systems/ESP32-DEVKITC-VE/12091812
and I have been able to program it by simply uploading with platformIO.

I just tried programming it with another laptop, and I had to press the Boot button every time I wanted to firmware to be programmed!
I thought that was just a matter of onboard circuitry, but clearly some settings differ between the laptops and one lets me program without pressing Boot??

Is this even possible? What could be the difference between the 2 laptops? I literally cloned my repo, so nothing was changed in the PIO folder.

Thanks!

Sounds a lot like A fatal error occurred: Failed to connect to ESP32 - Voltlog #357 - YouTube

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Seems as similar problem happens with ESP32 CAM MB programming boards. These boards seem to work with only ESP32 CAM modules that arrived with them but when using some other ESP32 CAM module then reset button on the MB doesn’t work (resetting with RTS signal in that case doesn’t work either).