This continuing education manual delivers an integrative synthesis of clinical and empirical literature focused on the rare comorbidity of obsessive-compulsive disorder (OCD) and antisocial personality disorder (ASPD). It highlights conceptual foundations, phenomenological tensions, pharmacotherapy challenges, psychological mechanisms linking incarceration to symptom exacerbation, and clinical implications for treatment adherence and therapeutic alliance. Using a detailed 18-week fluoxetine treatment case study as an empirical anchor, the manual emphasizes the importance of multi-method assessment, symptom-cluster intervention approaches, external reinforcement structures, and clinical coordination. It concludes by outlining current research gaps and future directions in this complex clinical area.