Each year, several thousand youth come under the jurisdiction of the Juvenile Justice Division of the Cook County Juvenile Court. The majority of these young people are still under compulsory school age, many have significant educational deficits, and virtually all have yet to complete high school. This report examines the educational options for court-involved youth in Chicago, how these options work, and the policy context within which schools and students operate. Data for the study were gathered through interviews with education and youth justice professionals and examination of policy reports and documents. One key finding is that educational options designed expressly for court-involved youth who are not incarcerated or detained are limited to transitional programs that grant neither a high school diploma nor a GED certificate. As a result, youth who wish to complete secondary education are expected to attend the same schools that also are used by young people who are not involved with the court. However, school accountability and zero-tolerance policies create incentives for schools to exclude low-performing or troublesome students. The findings raise serious concerns about how many court-involved youth return to the regular public schools—the only schools with the capacity to absorb them—and the availability of alternative educational programs for those youth who do not return.