The incapacity of individuals to experience empathy has long been linked to heightened risks of antisocial acts being perpetrated without remorse. Psychologists frequently consider deficits in empathy in the context of risk assessments and other clinical appraisals, such as the amenability to treatment. When evaluated, offenders—especially those with substantial psychopathic traits—may be motivated to mask their empathic deficits to avoid being characterized as callous and cold-blooded toward the victims of their crimes. The current study is the first known investigation with an offender population to simulate empathy via positive impression management (PIM). Using a mixed between- and within-subjects design, 81 male detainees were categorized into a Low, Moderate, or High Psychopathy group, based on the Psychopathy Checklist-Revised (PCL-R). For the within-subjects component, all offenders answered empathy questionnaires under genuine and PIM conditions. In the genuine condition, results indicate that offenders—irrespective of psychopathy—possessed cognitive empathy, but not affective empathy. In the PIM condition, offenders easily simulated high levels of empathy. Potential approaches to the assessment of simulated empathy in offender populations are explored, including a possible indicator for simulated affective empathy.