This brief is a compilation of lessons learned from the American Youth Policy Forum's (AYPF's) last two years of work focused specifically on systems-involved youth. Following a discussion about the education and workforce barriers these youth face, their outcomes, and the policies that affect them, this brief is organized into three key lessons that AYPF has identified as critical for promoting pathways to postsecondary education, training, and careers for youth involved in the juvenile justice system and/or youth in foster care. Drawing upon research-supported best practices of community-based programs from around the country, these lessons include: (1) Leveraging authentic youth voice; (2) Providing youth with a diversity of comprehensive supports and transitional services; and (3) Strategically aligning youth-serving systems and policies.