When it's not working, is Vcc actually at 3.3v? Measure it...
If you have a scope, put the scope on it. There's no black magic, and the only connection between the regulator and the Pico is through power and ground - so what's it doing to the power?
Espruino is a JavaScript interpreter for low-power Microcontrollers. This site is both a support community for Espruino and a place to share what you are working on.
When it's not working, is Vcc actually at 3.3v? Measure it...
If you have a scope, put the scope on it. There's no black magic, and the only connection between the regulator and the Pico is through power and ground - so what's it doing to the power?