This report details five lessons that emerged from Making the Shift Youth Homelessness Demonstration Lab‘s multi-year, collaborative project prototyping and testing approaches to help prevent and facilitate sustainable exits from youth homelessness. Key learnings in the report are organized into five categories: developing and refining program models; supporting communities to achieve Collective Impact; enabling technical training and assistance to build capacity; overcoming system and structural rigidity to support social R&D; and fostering a different kind of leadership. The report also highlights the success and challenges of the project’s Housing First for Youth, Family and Natural Supports, and Youth Reconnect program models, which were inspired by prevention approaches outlined in The Roadmap for the Prevention of Youth Homelessness.