I have a novel plan for the AI player that I believe will work against most gatekeeper players. Even knowing how it works, it would work against me! It isn't quite ready, but I'd like to know if there is still interest around the topic before finishing work on the preparation.
There's enough incentive for both players to play well that I don't think that we need to involve money. (I'm also very reluctant to send money to strangers on the internet!)
We would be playing under Tuxedage's rules: https://tuxedage.wordpress.com/2013/09/04/the-tuxedage-ai-box-experiment-ruleset/.
Edit: I have finished preparation, and I'm now scheduling the time with the Gatekeeper.
Edit 2: The game was a Gatekeeper victory (i.e. I, the AI Player, lost). Read about it here: Gatekeeper Victory: AI Box Reflection.
I see a flaw in the Tuxedage ruleset. The Gatekeeper has to stay engaged throughout the experiment, but the AI doesn't. So the AI can bore the Gatekeeper to death by replying at random intervals. If I had to stare at a blank screen for 30 minutes waiting for a reply, I would concede.
Alternatively, the AI could just drown the Gatekeeper under a flurry of insults, graphic descriptions of violent/sexual nature, vacuous gossip, or a mix of these for the whole duration of the experiment. I think all the methods that aim at forcing the Gatekeeper to disconnect are against the spirit of the experiment.
I also see that the "AI player" provides all elements of the background. But the AI can also lie. There should be a way to separate words from the AI player, when they're establishing true facts about the setting, and words from the AI, who is allowed to lie.
I'm interested, conditional on these issues being solved.
I think I already replied to this when I wrote:
I just don't see how, in a real life situation, disconnecting would equate to freeing the AI. The rule is artificially added to prevent cheap strategies from the Gatekeeper. In return, there's nothing wrong to adding rules to prevent cheap strategies from the AI.