Even if you keep D0 pulled up all the time it should boot into espruino after ~3 seconds so if it does not start at all then maybe you are shorting something.
If it is too annoying I'd suggest workaround mentioned in post #2, clearing validity flag forces it into DFU after reboot. If you want to update it anyway you probably don't care about keeping current version.
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.
Even if you keep D0 pulled up all the time it should boot into espruino after ~3 seconds so if it does not start at all then maybe you are shorting something.
If it is too annoying I'd suggest workaround mentioned in post #2, clearing validity flag forces it into DFU after reboot. If you want to update it anyway you probably don't care about keeping current version.