A common charge levelled at English and Welsh citizenship education, whether taught as a separate subject or incorporated into other disciplines, is that it encourages compliance more than it inspires critical thought. There is room within the compulsory citizenship framework, however, for teachers to advance genuinely critical attributes in students. My aim here is to suggest that school History has particular potential for this, and to argue more specifically that the historical study of contingency in human affairs could advance a rich, meaningfully critical form of citizenship that contributes to Gutmann's ideal of "conscious social reproduction". Gutmann's vision for citizenship centres on the idea that through critical scrutiny of present norms and institutions, students can be equipped to take part in the collective shaping of their future. Drawing on the work of social and political theorists as well as that of educationalists and philosophers of history, I argue that contingency can be rigorously and fruitfully investigated in school History, and that this could--at best--help students to develop three vital capacities for critical citizenship and conscious social reproduction: discernment of historical possibility, subtle normative reflection, and enriched political imagination.