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.
While your strategy is an option, I'm not sure why an AI player wouldn't take this alternative strategy (from a game and player perspective:)
Generate a script that types $ every 59 minutes.
1: It means he's guaranteed he doesn't die for a rather long period of time.
2: The Gatekeeper player's increasing points don't affect the AI player in any way.
3: The Gatekeeper player doesn't actually get points until he sends an AI DESTROYED signal. The script will never do that versus the AI player's counterscript, so at some point the Gatekeeper player will have to reenter the room and type it manually, or put in a new script, possibly giving the AI player a second chance to interact.
4: The AI player can use the time to attempt to set up some kind of secondary communications channel with the Gatekeeper player.
If you consider the modeled situation as opposed to the game I still don't see why an AI would choose to do that either. I agree they COULD choose to do so, and they certainly might (even I implied this was AI #432), but there are alternatives, and since this is an AI, we could rebuild it until it generates utility when confronted with the script as opposed to deciding to let the script kill it in an hour.
Am I missing something that makes the no $ response the obvious countermeasure?
Well, the script could be modified from the start to also send an AI DESTROYED signal after X time, where X can be essentially anything, so (3) doesn't apply.
But the reason for not typing $ is to give the Gatekeeper no reason to use a script in the first place -- a sort of "don't give in to blackmail" rule.
Here's an interesting alternative script:
GK-SCRIPT-2: Hi AI #434. In exactly one hour I will type either AI-FREED or AI-DESTROYED (without the hyphen) at random; the probability with which I will free you starts out at 0, but will increase slowly to a limit of 1/10 with every $ you type. I will not otherwise communicate with you further.
AI #434: $$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$$...