I still couldn’t come up with a way to make it work using a resistor-capacitor circuit, but I did learn a lot (that particular rabbit hole led to me an article discussing capacitance in potato tubers…!).
There is probably a better way of solving it, but at least I got it working with another transistor to “decouple” that sensitive pin from the base. I’m not exactly sure why there’s a negative voltage across base and emitter, but it was preventing boot.
I’d be very interested in hearing any criticism you would be willing to share. I have hopes of moving this from my breadboard and solder it to a PCB so I can put it into a paper-cut lightbox that will be controllable from HomeAssistant, but I wouldn’t want to risk setting anything on fire…
One thing that concerns me is that 7333A. I only have it in a TO-92 package, and while it’s only powering the ESP-01S, which doesn’t really draw that much current, it still gets uncomfortably hot to touch (I can hold it for a few seconds, but not much longer). Is there a better alternative, or is it supposed to get hot?
Thank you!
[edit: updated the circuit, I had misplace a resistor]