Transitional youth are young people ages 16 to 24 who leave foster care without being adopted or reunited with their biological families and/or who are involved in the juvenile justice system, where they may be in detention or subject to terms of probation. With childhoods often marked by trauma and a lack of stability, transitional youth face notoriously poor outcomes across many areas of life. Pay for success (PFS) may provide an opportunity to address some of the challenges faced by transitional youth and the difficulties in serving them. To further explore this opportunity, the Urban Institute initiated a Community of Practice, a collaborative of researchers, practitioners, and local government officials that came together to discuss the most pressing challenges facing youth aging out of foster care and/or involved in the juvenile justice system and the potential for PFS to fund programs that address these challenges. This brief summarizes insights drawn from Community of Practice conversations and provides recommendations for local governments, service providers, and other partners considering PFS as a tool for financing interventions serving transitional youth.