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Consider the situation where a word is chosen probabilistically from a finitelist. If an attacker knows the list and can inquire about each word in turn,then selecting the word via the uniform distribution maximizes the attacker'sdifficulty, its Guesswork, in identifying the chosen word. It is tempting touse this property in cryptanalysis of computationally secure ciphers byassuming coded words are drawn from a source's typical set and so, for allintents and purposes, uniformly distributed within it. By applying recentresults on Guesswork, for i.i.d. sources it is this equipartition ansatz thatwe investigate here. In particular, we demonstrate that the expected Guessworkfor a source conditioned to create words in the typical set grows, with wordlength, at a lower exponential rate than that of the uniform approximation,suggesting use of the approximation is ill-advised.

Brute force searching, the typical set and Guesswork