This study examines how probation officers’ (POs) knowledge of juveniles’ trauma influences probation practices. The study was conducted with POs who responded to a Web-based survey (n = 308). The POs were directed to randomly select one juvenile from their caseload and to complete the Probation Practices Assessment Survey to assess their knowledge of the youth’s lifetime trauma and past-year stressful life experience and their practice approaches. Nineteen percent of youths were reported as having had lifetime exposure to at least one type of trauma (for example, physical assault, sexual assault, witness violent death). The most common traumatic experience was sexual assault, with 11% of POs reporting this experience among the study youths. Structural equation modeling results indicated that POs’ knowledge of cumulative exposure to trauma is associated with treatment-oriented probation and counseling approaches. Results of this study signal the importance of careful assessments of exposure to trauma and stressful life events among youths on probation. The use of specialized trauma-informed assessment strategies also are recommended to increase the sensitivity of juvenile justice programs to trauma.