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Dostoevsky, Mandela, and others have long noted that prisons expose social realities, often hidden, particularly inequality and gaps between policy and practice. Prisons symbolize, mirror, and shape the communities and countries in which they exist. Although prisons informed and were intertwined with many of the defining moments of 1989, in the 20 years since, societies often failed to recognize the important role prison and punishment play in relationship to democracy. By not recognizing that “prison matters” in relationship to democracy, polities (whether in transition to democracy or established democracies) failed to adequately learn “prison lessons.” Starting with a case study of South Africa, this paper considers prisons during apartheid and under democratic governance. This case is connected to other comparative and international examples (including Russia, Brazil, and the USA) to identify five lessons learned and not learned concerning prison and democracy. First, policies and practices of imprisonment reflect social orders, especially structures of inequality and understandings of legitimate power and opposition. Second, countries transitioning to democracy seldom anticipate rising crime and invariably neglect the relevance of prisons. Third, nations do not adequately grapple with the role of prison in the past, especially the nondemocratic past. Fourth, in established and recent democracies, penal populism resulted as politicians defined prison as a solution to a host of social ills, ignoring the consequences of expanded punishment. Fifth, prisons shaped key substantive realities beyond their walls, from leadership to recidivism, scandals, fiscal deficits, and crises of legitimacy. [ABSTRACT FROM AUTHOR]