I stand corrected on the rules, but I think that's mainly Eliezer making it more difficult for himself in order to make it more convincing to the Gatekeeper player when Eliezer still wins. As he apparently did, but without actually playing against him we can only speculate how.
Keep in mind that, IIUC, Yudkowsky got to choose his opponents. He also decided to stop playing after he lost twice in a row, as Tuxedage apparently did as well.
I don't think there is any way the AI party can win against a competitive GK party. The AI can only win against a GK party willing to role-play, and this should be fairly trivial, since according to the rules the AI party has pretty much complete control over his fictional backstory and fictional world states.
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.