This article describes some experiential lessons and recommendations regarding supporting and evaluating comprehensive, multicomponent school and community-based initiatives for prevention of adolescent pregnancy. The lessons and associated recommendations were generated during small group retreats and individual meetings among initiative, university, and foundation staff, and during semistructured interviews with community-based staff and volunteers. This article outlines 15 recommendations associated with implementing, supporting, evaluating, and sustaining multicomponent school and community-based initiatives for prevention of adolescent pregnancy. These recommendations, if modified to fit community contexts, could help strengthen community efforts to prevent adolescent pregnancy. Given the controversial nature of teen pregnancy prevention programs, it is important to have insight, draw on the experiences of others, and avoid pitfalls associated with this work.