What is the minimum number of guesses needed on average to correctly guess a realization of a random variable? The answer to this question led to the introduction of the notion of a quantity called guesswork by Massey in 1994, which can be viewed as an alternate security criterion to entropy. In this paper, we consider guesswork in the presence of quantum side information, and show that a general sequential guessing strategy is equivalent to performing a single quantum measurement and choosing a guessing strategy based on the outcome. We use this result to deduce entropic one-shot and asymptotic bounds on the guesswork in the presence of quantum side information, and to formulate a semi-definite program (SDP) to calculate the quantity. We evaluate the guesswork for a simple example involving the BB84 states, and we prove a continuity result that certifies the security of slightly imperfect key states when the guesswork is used as the security criterion.
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