Transitional Justice discourses have largely focused on "paradigmatic transitions." Such analyses emphasize dealing with the human rights abuses committed by prior authoritarian or illegitimate regimes. But, authoritarian entities may not be the only kind of states with a legacy of serious and systematic rights-violations. A similar legacy may manifest in broadly democratic states that have experienced prolonged political violence. These "conflicted democracies" present a number of paradoxes, which come to the fore when peace and transitional political process are agreed, thereby providing unique challenges in political and legal transformation. This article explores these paradoxes and challenges. It further draws out a more nuanced understand of the transitional process by conceptually separating war/peace transitions from illiberal polity/democracy transitions.