The bluetooth one may not be related - but if it is I'd imagine it points to some issue with the Web IDE and Chrome.
What happens if you try and connect with Putty instead? Does it always work?
@Gordon started
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.
The bluetooth one may not be related - but if it is I'd imagine it points to some issue with the Web IDE and Chrome.
What happens if you try and connect with Putty instead? Does it always work?