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About this sequence of statements:

poweron_reset.on()
print('going to deepsleep')
utime.sleep_ms(10)
deepsleep()

Assuming you have the base of the NPN transistor at Pin 33 (I hope with a resistor), the emitter at GND and the collector at EN, the operation seems questionable. As soon as poweron_reset.on() is executed and Pin 33 is set to high, EN goes low and Pin 33 is going low immediately as well, resp is switched to input mode, switching the transistor off again. So the EN low pulse is very short and I do not know if the ESP32 is fully reset. If you see the output of the print statement, it's not.

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@davefes
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