Given a collection of strings, each with an associated probability of occurrence, the guesswork of each of them is their position in a list ordered from most likely to least likely, breaking ties arbitrarily. The guesswork is central to several applications in information theory: average guesswork provides a lower bound on the expected computational cost of a sequential decoder to decode successfully the transmitted message; the complementary cumulative distribution function of guesswork gives the error probability in list decoding; the logarithm of guesswork is the number of bits needed in optimal lossless one-to-one source coding; and the guesswork is the number of trials required of an adversary to breach a password protected system in a brute-force attack. In this paper, we consider memoryless string sources that generate strings consisting of independent and identically distributed characters drawn from a finite alphabet, and characterize their corresponding guesswork. Our main tool is the tilt operation on a memoryless string source. We show that the tilt operation on a memoryless string source parametrizes an exponential family of memoryless string sources, which we refer to as the tilted family of the string source. We provide an operational meaning to the tilted families by proving that two memoryless string sources result in the same guesswork on all strings of all lengths if and only if their respective categorical distributions belong to the same tilted family. Establishing some general properties of the tilt operation, we generalize the notions of weakly typical set and asymptotic equipartition property to tilted weakly typical sets of different orders. We use this new definition to characterize the large deviations for all atypical strings and characterize the volume of tilted weakly typical sets of different orders. We subsequently build on this characterization to prove large deviation bounds on guesswork and provide an accurate approximation of its probability mass function.

We explore properties and applications of the principal inertia components (PICs) between two discrete random variables X and Y. The PICs lie in the intersection of information and estimation theory, and provide a fine-grained decomposition of the dependence between X and Y. Moreover, the PICs describe which functions of X can or cannot be reliably inferred (in terms of MMSE), given an observation of Y. We demonstrate that the PICs play an important role in information theory, and they can be used to characterize information-theoretic limits of certain estimation problems. In privacy settings, we prove that the PICs are related to the fundamental limits of perfect privacy.

The guesswork problem was originally motivated by a desire to quantify computational security for single user systems. Leveraging recent results from its analysis, we extend the remit and utility of the framework to the quantification of the computational security of multi-user systems. In particular, assume that V users independently select strings stochastically from a finite, but potentially large, list. An inquisitor who does not know which strings have been selected wishes to identify U of them. The inquisitor knows the selection probabilities of each user and is equipped with a method that enables the testing of each (user, string) pair, one at a time, for whether that string had been selected by that user. Here, we establish that, unless U=V, there is no general strategy that minimizes the distribution of the number of guesses, but in the asymptote as the strings become long we prove the following: by construction, there is an asymptotically optimal class of strategies; the number of guesses required in an asymptotically optimal strategy satisfies a large deviation principle with a rate function, which is not necessarily convex, that can be determined from the rate functions of optimally guessing individual users' strings; if all users' selection statistics are identical, the exponential growth rate of the average guesswork as the string-length increases is determined by the specific Rényi entropy of the string-source with parameter (V-U+1)/(V-U+2), generalizing the known V=U=1 case; and that the Shannon entropy of the source is a lower bound on the average guesswork growth rate for all U and V, thus providing a bound on computational security for multi-user systems. Examples are presented to illustrate these results and their ramifications for systems design.

Consider the situation where a word is chosen probabilistically from a finite list. 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's difficulty, its Guesswork, in identifying the chosen word. It is tempting to use this property in cryptanalysis of computationally secure ciphers by assuming coded words are drawn from a source's typical set and so, for all intents and purposes, uniformly distributed within it. By applying recent results on Guesswork, for i.i.d. sources it is this equipartition ansatz that we investigate here. In particular, we demonstrate that the expected Guesswork for a source conditioned to create words in the typical set grows, with word length, at a lower exponential rate than that of the uniform approximation, suggesting use of the approximation is ill-advised.

How hard is it to guess a password? Massey showed that a simple function of the Shannon entropy of the distribution from which the password is selected is a lower bound on the expected number of guesses, but one which is not tight in general. In a series of subsequent papers under ever less restrictive stochastic assumptions, an asymptotic relationship as password length grows between scaled moments of the guesswork and specific Rényi entropy was identified. Here, we show that, when appropriately scaled, as the password length grows, the logarithm of the guesswork satisfies a large deviation principle (LDP), providing direct estimates of the guesswork distribution when passwords are long. The rate function governing the LDP possesses a specific, restrictive form that encapsulates underlying structure in the nature of guesswork. Returning to Massey's original observation, a corollary to the LDP shows that expectation of the logarithm of the guesswork is the specific Shannon entropy of the password selection process.