Although students with disabilities are over-represented in the juvenile justice system and frequently receive poor educational services, few studies have examined strategies to increase compliance with student needs and individualized education programs. In this study, we conducted interviews with eight probation officers in the Advocacy Unit of a juvenile justice system in a large Midwestern city. We examined the advocacy strategies used by the probation officers as well as the barriers they faced in ensuring court-involved youth received appropriate educational supports. Advocacy strategies included: documentation, collaboration with other stakeholders, and assertive but not aggressive communication. Probation officers also mentioned more creative advocacy strategies. Barriers to effective advocacy included: poor working relationships with schools, older age of youth, and obstacles to parent involvement. We discuss implications for research and practice.