I realise that it isn't polite to say that, but I don't see sufficient reasons to believe you. That is, given the apparent fact that you believe in the importance of convincing people about the danger of failing gatekeepers, the hypothesis that you are lying about your experience seems more probable than the converse. Publishing the log would make your statement much more believable (of course, not with every possible log).
(I assign high probability to the ability of a super-intelligent AI to persuade the gatekeeper, but rather low probability to the ability of a human to do the same against a sufficiently motivated adversary.)
We played. He lost. He came much closer to winning than I expected, though he overstates how close more often than he understates it. The tactic that worked best attacked a personal vulnerability of mine, but analogues are likely to exist for many people.
Update 2013-09-05.
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.