This paper explores some of the key issues and challenges facing program and city leaders in creating and sustaining afterschool program opportunities that engage the interest and participation of high school-age youth. The authors discuss effective program characteristics and strategies for citywide collaboration, along with steps for cities and organization to build their capacity to meet the needs of today's teen youth during the out-of-school time hours. Investigation was particularly focused on five cities: Baltimore, Chicago, Denver, Kansas City, and Fort Worth.