Educational pathways in colonial and postcolonial spaces often range far beyond the classroom. Reconstructing histories of this wider terrain of education reveals long-running arguments over what types of new knowledge might be most useful for living well amid war and within fast-changing colonial and postcolonial states. These debates over the provision of useful knowledge—including military, mechanical, linguistic, and religious training—are a window into how people have discussed changing ideas of authority, class mobility, and the future. We trace a wider terrain of education in southern (now South) Sudan, where education histories have generally either focused on a handful of mission-founded formal schools or hagiographies of powerful military men with PhDs. Drawing on archival evidence and interviews gathered in South Sudan since 2019, we argue that histories of education in colonial and postcolonial Africa are crucial to understanding intellectual histories in everyday life.