Engagement between higher education and other societal sectors is a key theme in higher education discourse in South Africa, as it is in other countries. In South Africa, however, engagement has gained additional status as an appropriate strategy for pursuing African Scholarship. On the ground, however, inequitable power relationships and erratic participation have posed serious challenges to the effectiveness and sustainability of engagement initiatives. From the experiences of seven South African academics and the local community members and service-providers with whom they engaged in service-learning, three factors emerged as mediating the power/participation dynamic of their engagement. The impact of these factors, namely, structure, meaning, and place and time, are discussed, leading to the conclusions that scholarly engagement requires ideological and practical support from higher education institutions and further study in South African contexts.