While transitional justice, domestic and international, has been the subject of an expansive literature, particularly since the political transitions of the 1990s, until recently it has not been a topic of direct interest to international relations (IR) scholars or theorists.1 However, recent books and articles have begun to examine the challenges of transition, and specifically the virtues and vices of prosecutions and other punitive forms of accountability, through the lenses of theories of international relations, such as realism, liberalism, and constructivism.2 Theorists have attempted to transform theories of systems, structures, and agencies in international politics, then, into ones that can help to describe the workings and needs of polities after significant violence and atrocities. In this chapter, we will briefly discuss the insights of each of these theories, before turning to a specific case, that of the peace process and hybrid tribunal in Sierra Leone. What we find is that key insights from realism, couched as pragmatism, are of great importance in addressing the needs of transitional societies. However, we argue that realism, like the other theories, does not take a nuanced view of security. Specifically, while a core dilemma for transitional societies is that punishment for past gross human rights abuses may generate instability by provoking retaliation, particularly by armed groups or state security forces, none of these theories seriously engage in consideration of how to prevent or control reactions by these groups in the short and long term. That said, the UN and other actors supporting transitions to peace recognize the importance of accountability for past crimes notwithstanding possible destabilizing effects that this might have. What is vital, then, is to fashion peacebuilding strategies that can achieve accountability while simultaneously limiting the likelihood of instability. This requires going beyond any simple “justice versus peace” dichotomies.