Have you checked the troubleshooting page? This particular entry sounds exactly like what you're describing:
There are also entries for connectivity issues on there (in case you haven't seen them already).
And when you say CLI, do you mean the Web IDE? Just making sure...
No, when I write CLI, i mean the npm espruino, that you can use from the terminal. I can't contact the watch from the web IDE, since I can't enable bluetooth, however the trick with holding btn 1 after reboot show the MAC address and you can use
espruino -p MAC address
In that way you can install js code.
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