A structured comparative analysis of one post-authoritarian case (Uruguay), two post-conflict cases (Rwanda and Angola), and one mixed case (Peru) demonstrates that contextual factors and timing are crucial to understanding how trials, truth commissions, reparations, and amnesties can affect the prospects for peace and democracy. We highlight the importance of pre-conflict violence, the nature of the conflict and how it ended, previous experience with democracy, regional legal and institutional frameworks, and the role of international actors in shaping the prospects for peace and democracy.