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Morendil comments on Discussion: Yudkowsky's actual accomplishments besides divulgation - Less Wrong
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The record of AI box experiments (those involving Eliezer) is as follows:
The last three experiments had bigger (more than 2 orders of magnitude, I think) outside cash stakes. I suspect Russell and D. Alex may have been less indifferent about that than me, i.e. I think the record shows that Eliezer acquitted himself well with low stakes ($10, or more when the player is indifferent about the money) a few times, but failed with high stakes.
Which suggests to me that as soon as people actually feel a bit of real fear- rather than just role-playing- they become mostly immune to Eliezer's charms.
With an actual boxed AI though, you probably want to let it out if it's Friendly. It's possibly the ultimate high stakes gamble. Certainly you have more to be afraid of than with a low stakes roleplay, but you also have a lot more to gain.