There is a growing body of research demonstrating that the therapeutic alliance (TA) affects outcomes among specialized forensic populations, including sexual offenders. Despite this consensus, researchers continue to question whether higher levels of psychopathic traits are conducive to the formation of a therapeutic relationship for high-risk sexual offenders. Thus, the current study adds to the literature by examining the relationship between the TA and levels of psychopathy among a sample of incarcerated sexual offenders participating in sexual offender treatment. Overall, we found no significant relationships between Psychopathy Checklist–Revised (PCL-R) scores and the Working Alliance Inventory (WAI) for either client or therapist ratings. However, when we excluded those offenders who were participating in aftercare, a significant negative relationship was found between client ratings of the Bonds subscale and PCL-R total scores. Next, after controlling for risk and group status (aftercare/non-aftercare), we found no significant differences between either client or therapist total WAI scores when compared by level of psychopathy as measured by the PCL-R (low, >20; moderate, 20-30; and high, >30). Furthermore, when Factor 1 and Factor 2 scores of the PCL-R were examined individually, neither factor significantly predicted either client or therapist total WAI score after controlling for risk and group status. Findings are discussed as they pertain to the treatment of sexual offenders with elevated levels of psychopathic traits.