As the correctional population continues to increase, probation agencies struggle to adequately supervise offenders with unique needs, including those with mental disorders. Although more than 100 U.S. probation agencies have implemented specialty mental health case-loads, little is known about their practices. Based on detailed observations of 83 audio-taped meetings, we examined interactions between probationers and officers in a prototypic specialty agency, focusing on the extent to which practices comport with evidence-based risk reduction principles. We found that specialty officers (a) more frequently discussed probationers’ general mental health than any individual criminogenic need, (b) chiefly questioned, directed, affirmed, and supported (rather than confronted) probationers, and (c) relied more heavily on neutral strategies and positive pressures (e.g., inducements) rather than negative pressures (e.g., threats of incarceration) to monitor and enforce compliance. Implications for “what works” to promote community integration for probationers with mental disorders are discussed.