The study described in this article highlights the complexity of service-learning efforts and community engagement pursuits. It is based on 6.5 months of qualitative fieldwork in International Baccalaureate international schools in Kenya, Ethiopia, and South Africa. The article unpacks the understandings and skills involved in service-learning efforts through a framework developed by the research. The framework includes six knowledge domains: service-learning pedagogy, global issues, school contexts, local contexts, leadership/organizations, and communication. The author argues that related competencies in these domains support efforts, whereas related knowledge gaps impede efforts. Such a framework allows teams to be self-reflective and intentional, justifies related resources, and explains the strain that educators involved in these pursuits can feel. The author argues that facilitators need to have deep knowledge in far more than service-learning pedagogy.