Delivering reentry services to youth proves challenging. This brief describes the implementation and sustainability of two Juvenile Second Chance Act reentry programs in Oklahoma and Virginia. Drawing from semi-structured interviews with grantees and community and state stakeholders conducted between 2013 and 2016, evaluators document the challenges to providing prerelease support and coordinating services among institutional and community supervision agencies and organizations. This brief is part of a larger evaluation of Juvenile Offender Reentry Demonstration Projects funded by the Office of Juvenile Justice and Delinquency Prevention in fiscal year 2010.