This study was designed to test the hypothesis that individuals with antisocial, particularly violent, histories of offending behavior have specific problems in social cognition, notably in relation to accurately envisioning mental states. Eighty-three male offenders on community license, 65% of whom met the threshold for antisocial personality disorder (ASPD), completed a battery of computerized mentalizing tests requiring perspective taking (Perspectives Taking Test), mental state recognition from facial expression (Reading the Mind in the Eyes Test), and identification of mental states in the context of social interaction (Movie for the Assessment of Social Cognition). The results were compared with a partially matched sample of 42 nonoffending controls. The offender group showed impaired mentalizing on all of the tasks when compared with the control group for this study when controlling for demographic and clinical variables, and the offending group performed poorly in comparisons with participants in published studies, suggesting that limited capacity to mentalize may be part of the picture presented by individuals with histories of offending behavior. Offenders with ASPD demonstrated greater difficulty with mentalizing than non-ASPD offenders. Mentalization subscales were able to predict offender status and those with ASPD, indicating that specific impairments in perspective taking, social cognition, and social sensitivity, as well as tendencies toward hypomentalizing and nonmentalizing, are more marked in individuals who meet criteria for a diagnosis of ASPD. Awareness of these deficits may be helpful to professionals working with offenders, and specifically addressing these deficits may be a productive aspect of therapy for this "hard to reach" clinical group.