The Opportunity Works initiative, led by Jobs for the Future (JFF) in collaboration with the Aspen Institute Forum for Community Solutions, works to bring together a cross-sector collaborative in specific communities to improve outcomes for young people, with special attention paid to those who are homeless, and in or transitioning from the foster care and/or juvenile justice systems. In this report, JFF highlights lessons learned from the initiative, based on the “Back on Track” model, to reconnect opportunity youth and guided by JFF coaching to local anchor organizations and service providers. The authors also describe the complex nature of what it takes to reach these positive results and the many interlocking pieces that are part of the solution. (author abstract modified)