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The two-envelope switching trap

Two sealed envelopes are on the table. One holds exactly twice as much money as the other, but you do not know which is which. You pick one envelope and hold it, unopened. Then you reason:

"Let my envelope hold AA dollars. The other envelope is equally likely to hold 2A2A or A/2A/2, so its expected value is 12(2A)+12(A2)=54A\tfrac12(2A) + \tfrac12\left(\tfrac{A}{2}\right) = \tfrac{5}{4}A, which is more than AA. I should switch."

But after switching you could relabel the new envelope's amount and run the same argument, telling you to switch back, forever.

Explain what is wrong with this reasoning.

Your answer

This one is open-ended. Work it through, then check your reasoning against the full solution.

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