The education provided to youth in detention and juvenile corrections facilities may be the last opportunity for these youth to reconnect with learning and graduate from high school. A large percentage of youth who exit these facilities do not return to school. Dropping out is associated with a number of negative outcomes, including higher rates of unemployment, lower-paying jobs, dependence on welfare, and incarceration in adult prisons. Although research has shown that academic achievement is associated with a reduction in recidivism rates, youth seldom re-engage in school after release from commitment programs. This article discusses the application of the educational framework Universal Design for Learning (UDL), to transform the education that is provided to incarcerated youth. UDL is an educational framework that helps educators plan for flexibility with respect to teaching methods, materials, and technologies. Contrasting current practices in detention and juvenile corrections facilities with UDL-informed strategies, the authors describe how the three UDL principles (multiple means of representation, multiple means of student action and expression, and multiple means of student engagement) can help educators design classroom environments that address the educational needs of incarcerated youth more effectively. The article highlights the application of UDL in the context of five areas: curriculum and instruction, assessment, behavior, transition planning, and teacher preparation. It is argued that the UDL framework has the potential to improve the poor quality of education currently provided in detention and juvenile corrections facilities and to help incarcerated youth become more engaged in learning, an important factor contributing to their successful reintegration into school and the community.