ArisKatsaris comments on I attempted the AI Box Experiment (and lost) - Less Wrong
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Going with the "dead loved one" idea mentioned above, the AI says a line that only the Gatekeeper's dead child/spouse would say. That gets them to pause sufficiently in sheer surprise for it to keep talking. Very soon the Gatekeeper becomes emotionally dependent on it, and can't bear the thought of destroying it, as it can simulate the dearly departed with such accuracy; must keep reading.