In this paper, we consider the problem of guessing a sequence subject to a distortion constraint. Specifically, we assume the following game between Alice and Bob: Alice has a sequence $\bx$ of length $n$. Bob wishes to guess $\bx$, yet he is satisfied with finding any sequence $\hat{\bx}$ which is within a given distortion $D$ from $\bx$. Thus, he successively submits queries to Alice, until receiving an affirmative answer, stating that his guess was within the required distortion. Finding guessing strategies which minimize the number of guesses (the \emph{guesswork}), and analyzing its properties (e.g., its $ρ$--th moment) has several applications in information security, source and channel coding. Guessing subject to a distortion constraint is especially useful when considering contemporary biometrically--secured systems, where the "password" which protects the data is not a single, fixed vector but rather a \emph{ball of feature vectors} centered at some $\bx$, and any feature vector within the ball results in acceptance. We formally define the guessing problem under distortion in \emph{four different setups}: memoryless sources, guessing through a noisy channel, sources with memory and individual sequences. We suggest a randomized guessing strategy which is asymptotically optimal for all setups and is \emph{five--fold universal}, as it is independent of the source statistics, the channel, the moment to be optimized, the distortion measure and the distortion level.