Are you talking about updating firmware or updating the current espruino script?
If it is the latter, the telnet module allows you to connect via ip, so if the GSM is up, you should be able to connect the in the web i.e., connect via the ip rather than serial.
Sorry, I have only tested on the esp8266 (in which the wifi is always connected). With GSM I guess you'll need to have oninit() that will see that network up. I'm also unsure on how you would know what ip it is on - perhaps you could get it to send that to a website via a http get?
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