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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.
@allObjects
...did you ever verify the quality of mechanical/electrical connection of your USB cable / connectors? ...moving things physically while uploading - can even just be typing - bothers bad / low-quality connections. Also the way code is written can impact the upload process... any upload process, because Espruino executes JavaScript - or you do other (crazy) things on you Win box - it is not just a source / file / byte transfer - and when something is done that keeps Espruino for too long too busy - or you do other (crazy) things on you Win box -upload / communication timing between uploader and Espruino may fall apart... Also what else in regard to 'electro smog' is going on in your environment can have an impact.
...and after all, non-Gordon boards are of various reliability...
PS: forgot to mention that Espruino Web IDE has a Settings - Communication - Throttle Send that could help you...