Andreas_Giger comments on Can anyone explain to me why CDT two-boxes? - Less Wrong Discussion
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I agree if you say that a more accurate statement would have been "omniscient Omega entails either backwards causality or the absence of free will."
I actually assign a rather high probability to free will not existing; however discussing decision theory under that assumption is not interesting at all.
Regardless of the issue of free will (which I don't want to discuss because it is obviously getting us nowhere), if Omega makes its prediction solely based on your past, then your past suddenly becomes an inherent part of the problem. This means that two-boxing-You either has a different past than one-boxing-You and therefore plays a different game, or that Omega makes the same prediction for both versions of you, in which case two-boxing-You wins.
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.