For youth who are the most vulnerable to challenging community conditions, more limited opportunities, and poor health, educational and economic trajectories derive especially strong benefits from engagement in community youth development efforts. Although communities can benefit in powerful ways from the knowledge and insight of these youth populations, the experiences of vulnerable youth are often underrepresented in planning and decision making. This article draws on lessons learned from two communities that successfully engaged such youth in a community change initiative over four years. Key elements in creating the types of safe, supportive, and meaningful settings that promote young people's ongoing participation and leadership were intentionality and commitment; local knowledge of vulnerable populations; adult allies with key capacities; meaningful focus; resources for intensive outreach, relationship building, and youth support; and continuity of key adults. Each of these elements is described, identifying the ways they build on often underrecognized forms of social capital and offering lessons learned about engaging underserved youth populations in community youth development.