The Center for Alternative Sentencing and Employment Services (CASES) has developed a model for overcoming barriers to school reentry by building partnerships between the justice and education systems in New York City. This paper presents three programs developed through CASES to help court-involved youth continue their education and reenter their communities. The Committee on Court-Involved Students was formed in 2001 and includes professionals from the city’s juvenile justice and education systems who work together to identify and remove barriers to education for students leaving custody. The School Connection Center is a high school admissions office whose staff of criminal justice and education professionals work together to ensure that education reentry goals are met for students discharged from custodial schools to residences in Manhattan. The Community Prep High School is a transitional school that addresses the academic and social needs of students who are not ready to attend community schools on release from custody. Preliminary data from these programs show that partnerships between the justice and education systems are essential for juvenile reentry and that they must provide remedies for two critical gaps: delayed access to community schools and a shortage of appropriate schools for young people leaving custody.