The purpose of this chapter is to help school leaders understand the political ecology of schooling specifically focused on the complex interconnectedness of schools and other social service agencies. It examines the complex interactions of external communities and schools and discusses how principals can maximize the benefits of community engagement while understanding the potential pitfalls of such engagement. The chapter also describes the benefits of creating a sense of community within schools and provides suggestions on ways principals can make schools more welcoming. By reading this chapter and completing the related field assignments, school leaders should be better prepared to dive into the messy political arena of community engagement and hopefully develop new pathways to improve the lives of at-risk children.