Despite generations of struggle to secure democracy and universal citizenship rights in South Africa, the first post-Apartheid generation has been shown to be, if anything, less likely to embrace democracy and active citizenship, and to be more susceptible to intolerance than those in generations socialized under Apartheid’s rigid racial boundaries and sharply circumscribed rights. Though surveys have shown that education is a strong driver of democratic support in other African countries, recent studies show no comparable effects for those in South Africa’s “Born Free” generation, even though they are being socialized amidst unprecedented economic opportunities and within the nation’s first free, public education. This has important theoretical implications, as South Africa stands in marked contrast to nations such as West Germany, Japan and Spain, where purpose-built civics curricula imbued their post-authoritarian generations with critical, democratic skills and a culture of participation. This failure of one of the world’s highest-profile emergent democracies to instil a new, democratic citizenship raises significant questions about the roles of education and political socialization in the building of democracy. We use an original, 2012 representative-sample survey of 2500 high school students and 80 teachers from 45 schools in metropolitan Cape Town to explore the attitudes of students and teachers toward schools’ civics learning schemes and toward democracy and the democratic process more generally. Among other hypotheses, we test whether history classes and the newly instituted Life Orientation classes are related to greater political knowledge and more positive democratic norms. We also examine the role of family background, race, economic conditions and socio-political experiences in students’ perceptions of South Africa’s political system and their role in it. Altogether, we explore whether the education of the nation’s young can impart a critical, engaged democratic citizenship, despite the ongoing vicissitudes of unemployment, political divisions and social uncertainty.