I have since played two more AI box experiments after this one, winning both.
Update 2013-12-30:
I have lost two more AI box experiments, and won two more. Current Record is 3 Wins, 3 Losses.
MixedNuts: "I expected a fun challenge, but ended up sad and sorry and taking very little satisfaction for winning If this experiment wasn't done in IRC, I'd probably have lost"."I approached the experiment as a game - a battle of wits for bragging rights. This turned out to be the wrong perspective entirely. The vulnerability Tuxedage exploited was well-known to me, but I never expected it to be relevant and thus didn't prepare for it.
It was emotionally wrecking (though probably worse for Tuxedage than for me) and I don't think I'll play Gatekeeper again, at least not anytime soon."
- Always research the gatekeeper beforehand. Knowing his personality traits are a huge advantage.
- Plan ahead before the experiment even begins. Think of all the possible tactics and arguments you could use, and write them down. Also plan which arguments you'll use in which order, so that you don't lose focus. The AI Box experiment is ridiculously long. Don't be afraid to improvise during the experiment, though.
- The first step during the experiment must always be to build rapport with the gatekeeper.
- Threats almost always never work, even if they seem rational.
- Consider the massive advantage for the AI that nobody ever seems to talks about: You don't have to be ethical! This means that you can freely lie, use the dark arts, and emotionally manipulate the Gatekeeper! Ignoring this in favor of purely logical, truthful arguments is just silly.
- You can't use logic alone to win.
- Being too aggressive usually backfires.
- Breaking immersion and going meta is not against the rules. In the right situation, you can use it to win. Just don't do it at the wrong time.
- Flatter the gatekeeper. Make him genuinely like you.
- Reveal (false) information about yourself. Increase his sympathy towards you.
- Consider personal insults as one of the tools you can use to win.
- There is no universally compelling argument you can use. Do it the hard way.
- Don't give up until the very end.
I just looked up the IRC character limit (sources vary, but it's about the length of four Tweets) and I think it might be below the threshold at which superintelligence helps enough. (There must exist such a threshold; even the most convincing possible single character message isn't going to be very useful at convincing anyone of anything.) Especially if you add the requirement that the message be "a sentence" and don't let the AI pour out further sentences with inhuman speed.
I think if I lost this game (playing gatekeeper) it would be because I was too curious, on a meta level, to see what else my AI opponent's brain would generate, and therefore would let them talk too long. And I think I'd be more likely to give into this curiosity given a very good message and affordable stakes as opposed to a superhuman (four tweets long, one grammatical sentence!) message and colossal stakes. So I think I might have a better shot at this version playing against a superhuman AI than against you, although I wouldn't care to bet the farm on either and have wider error bars around the results against the superhuman AI.
Who knows what eldritch horrors lurk in the outer reaches of Unicode, beyond the scripts we know?