This article presents a multidimensional model of engagement (i.e., behavioral, emotional, cognitive) across school and organized out-of-school contexts (i.e., extracurricular activities, community organizations, and after-school programs). First, I describe the reasons why it is important to examine engagement in both school and organized out-of-school contexts. Next, an outline of the different ways involvement in organized out-of-school activities may relate to school is given. Finally, I present a conceptual model that outlines the contextual factors that are related to higher engagement in both school and out-of-school settings. The impact of teacher support, peer relationships, structure, and task characteristics on engagement are outlined. Practical examples of ways teachers can increase engagement in each area are given. (Contains 1 figure.)