Several recent studies report that punished individuals appear more likely to offend in the future and believe that the certainty of punishment is lower than do their less punished/unpunished counterparts. This article investigates two competing explanations for the latter finding. Under the selection account, punishment simply identifies the most committed offenders whose certainty estimates, even following punishment, remain lower than those of less committed offenders. The second account, resetting, invokes a judgment and decision-making bias known as the “gambler’s fallacy.” Under this explanation, punished offenders reset their sanction certainty estimate, apparently believing they would have to be exceedingly unlucky to be apprehended again. Herein, we report a preliminary empirical investigation of these explanations and address the challenge to contemporary deterrence theory posed by the “positive punishment effect.