Now what I really want to see is an AI-box experiment where the Gatekeeper wins early by convincing the AI to become Friendly.
Not quite the same, but have you read Watchmen? Specifically, the conversation that fvyx fcrpger naq qe znaunggna unir ba znef. (Disclaimer: it's been a while since I read it and I make no claims on the strength of this argument.)
AI Box Experiment Update #3
Tuxedage (AI) vs Alexei (GK) - Gatekeeper Victory
Tuxedage (AI) vs Anonymous (GK) - Gatekeeper Victory
I have won a second game of AI box against a gatekeeper who wished to remain Anonymous.
This puts my AI Box Experiment record at 3 wins and 3 losses.