Qiaochu_Yuan comments on I attempted the AI Box Experiment (and lost) - Less Wrong
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As I mentioned in another comment, these strategies are consistent with the idea of "traumatic bonding," the psychological mechanism that powers Stockholm syndrome and keeps people in abusive relationships. The large number of people who stay in abusive relationships seems like good evidence to me that this is a generally effective way to emotionally hack a human.
You also may not be interpreting "personal insult" the way I'm interpreting it. I'm not thinking of a meaningless schoolyard taunt but something that attacks an actual insecurity the gatekeeper has.