Envelopes with Numbers

You are given 2 sealed envelopes with numbers inside. You are told that one of the numbers is twice as much as the other one. You grab one of the envelopes and right before you open it, you make the following calculation:

“If this envelope contains X inside, then the other envelope contains either X/2 or 2X inside. Since the chance that the other envelope contains a larger number is exactly 50%, the expected money I will get after switching is X/4 + X = 1.25X > X. Therefore, I should switch!”

Clearly, this reasoning is wrong, since you can’t possibly deduce which envelope of the two contains a larger number. Where is the mistake?

The trick is that conditionally on the fact that your envelope contains X, it is not true that the other envelope has 50% chance of containing either X/2 or 2X. The reason is that it is impossible that all amounts of dollars appear in the envelopes with the same probabilities (densities). Thus, for example, if it is very unlikely that an envelope contains more than 1000, and you open an envelope with 800 inside, you will not think that the other envelope has 50% chance of containing 1600.

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