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By Andrew Grande
#39252 Thanks for suggestions, I went on to review all of the source code (sizable by now) and found that my OLED display (SSD1306) declared GPIO16 as a reset pin in its constructor.

No idea where it's used, but changing it to any other free pin seemed to have worked. I can now wire GPIO16 and RST directly and keep the whole board working fine :)
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By OzFlipper
#41153 I know you solved your problem, but another few things for others who may read this thread to consider...

Unplug your USB and reset (yes, you'll need external power), and make sure nothing else is on GPIO16 or GPIO0, and that GPIO16 is connected to reset.

If you are using a NodeMCU board or anything else that uses the USB serial to drive the reset (and program) pins then the port can sometimes hold the reset high, stopping GPIO16 from resetting the board properly. It can also hold the program pin high, so if it does reset it goes into the bootloader instead of the application code.

Common issue, one that drove me batty when I did my first project that used deep sleep.

Phil.