Desrtopa comments on Can anyone explain to me why CDT two-boxes? - Less Wrong Discussion
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Two-boxing-you is a different you than one-boxing-you. They make different decisions in the same scenario, so something about them must not be the same.
Omega doesn't make its decision solely based on your past, it makes the decision based on all information salient to the question. Omega is an omniscient perfect reasoner. If there's anything that will affect your decision, Omega knows about it.
If you know that Omega will correctly predict your actions, then you can draw a decision tree which crosses off the outcomes "I choose to two box and both boxes contain money," and "I choose to one box and the other box contains no money," because you can rule out any outcome that entails Omega having mispredicted you.
Probability is in the mind. The reality is that either one or both boxes already contain money, and you are already going to choose one box or both, in accordance with Omega's prediction. Your role is to run through the algorithm to determine what is the best choice given what you know. And given what you know, one boxing has higher expected returns than two boxing.