Hmm, that's really odd. As other have said a capacitor might help, but I thought I'd put some reasonable caps on-board to try and account of that.
@allObjects suggestion of wifi.at.debug() is definitely worth trying as the ESP8266 might be trying to say something.
Other thing I can think (which might be backed up by wifi.at.debug() is that if the board is dirty around the contacts, GPIO0 on the ESP8266 might be getting pulled down to 0v (you could try shorting it to 3.3v?) and the ESP8266 could be entering bootloader mode rather than WiFi mode.
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