In May 2000, the United States Department of Labor awarded sizable Youth Opportunity (YO) Grants to 36 high-poverty urban, rural, and Native American communities. These communities were among the most economically distressed communities in the nation, all characterized by high drop out rates, high youth unemployment rates, greater incidence of juvenile crime, violence, and gang activity. The Youth Opportunity Grants--ranging from $3.1 to $43.8 million over five years--provided the resources to put in place comprehensive approaches at considerable scale. The Department's expressed intent in awarding these grants was to demonstrate that the educational outcomes and economic prospects for young people in high-poverty communities could be dramatically improved by infusing these communities with resources; building capacity and infrastructure; connecting systems; and developing comprehensive, age-appropriate opportunities for youth. The observations in this paper are based on the responses of 22 of the YO sites to a "Learning from Youth Opportunity" survey administered by the Center for Law and Social Policy (CLASP), wherein respondents were asked to identify areas of strength and challenges on 120 items in four categories: (1) Mobilizing and Engaging Leadership; (2) Connecting Systems; (3) Implementing Comprehensive Program Strategies; and (4) Engaging the Business Sector. Focus group discussions were conducted with several of the YO sites shortly after the start of the final grant year and then again as the year ended. This paper presents an assessment of the capacity building efforts in YO communities, the strengths and challenges of the program, lessons learned, and recommendations for policy and approach. The following are appended: (1) YO Community Collaborations with Other Systems; (2) Communities Indicating Success Worth Sharing in Various Areas; and (3) Contact Information for Respondents to the "Youth Opportunity: Lessons Learned Survey."