In this article, two service-learning practitioners reflect on the development of the pedagogy of service-learning within higher education in two different contexts: the United States and South Africa. They examine and compare service-learning’s evolution in these two different, distant parts of the world from the vantage points of their long involvement in this work, noting the institutional locations and motivations of early pioneers and the important, often enabling influence of higher education’s social context. They conclude with theory-building speculation on how these service-learning stories may illuminate some of the complexities of institutional change in higher education.