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Cryptography

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    $\begingroup$ The context for the question is passwords in the face of attacks, as covered very well by Thomas' answer. As noted in Entropy (information theory), entropy is defined in the context of a probabilistic model. Clearly we should expect that an attacker is going to use a smart probabilistic model, so it is indeed the case that English words have less useful entropy in a password context than the same letters in a different order. We need to use more than the original "Shannon entropy", which has a different set of assumptions. $\endgroup$ Commented Dec 16, 2014 at 18:11