Developed with the goal of preventing recidivism, contemporary sex offender supervision models focus on collaboration between probation officers and therapists. This exploratory study used focus groups to examine the working relationships between probation officers and therapists from two large U.S. urban probation departments. Overall, both probation officers and therapists were quite positive about their working relationships; they valued each others’ roles and agreed that regular, accurate, and timely communication occurred frequently. Not all relationships, however, were effective. Several probation officers and therapists expressed dissatisfaction with poor communication, conflicts between the goals of therapy and probation, a lack of resources, and deficits in the policies they needed to adequately implement components of their supervision model (the containment model). Our findings suggest ways to structure sexual offender supervision that integrate the distinct orientations of probation officers and therapists into a collaboration that promotes public safety and work well for all.