It might be that on Windows the secure connection is causing problems. I recently (yesterday!) had someone with what appears to be similar connection problems with 1v95 on Windows, so I'm wondering if it's a windows update that broke something - I hadn't noticed similar reports before.
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.
Ok, just some other thoughts...
As you seem to have it connecting better with 1v93, you could try using the advice in http://forum.espruino.com/conversations/303637/ and see if that helps you at all.
You could also see if you have more success trying this method of connecting: https://github.com/espruino/EspruinoHost#usage
It might be that on Windows the secure connection is causing problems. I recently (yesterday!) had someone with what appears to be similar connection problems with 1v95 on Windows, so I'm wondering if it's a windows update that broke something - I hadn't noticed similar reports before.