This article examines how different histories and contexts of political and educational change in Botswana and South Africa have shaped the more regular classroom practice observed in Botswana. It does this through an interpretive synthesis and comparison of four key moments of educational change in Botswana and South Africa during the twentieth century, followed by an examination of more recent curriculum and assessment, teacher education, supervision, and evaluation policy in each country. The article highlights differences in decolonization processes and similarities in economic conditions and spending on education. It shows that processes of educational change have been and continue to be marked by the respectively different histories of gradual and incremental change on the one hand, and rapid, disruptive change on the other. And while recent curriculum and assessment policies show convergence with one another, this is less the case with teacher policies and processes.