This article presents six potential roles played by principals after school, exploring why each is important and how each can be challenging. Can what is known about effective principal leadership be applied to afterschool program management, leadership, and implementation? Since the role of the principal in school sites is central, while afterschool program models are diverse, how can we engage in useful dialogue about principal involvement after school? Investigation of these questions in the existing literatures on principal leadership and afterschool programming is limited. Believing that afterschool programs must be tailored to the distinct needs of school sites, the author hopes principals and afterschool program staff can use the framework presented in this article as a practical tool with which to understand and delegate roles, thereby increasing the success of their programs. For staff working in programs at community based organizations, this framework may be useful in designing and assessing program leadership structures and designating responsibilities.