Transitional justice – i.e., how societies respond to the legacies of massive and systematic human rights violations – has become an important scholarly field as well as a political and legal terrain of concern and contestation. The role of courts in the larger picture of transitional justice is particularly contentious and judicial behaviour in these contexts is under-explored. The aim of this chapter is therefore two-fold. First, it maps out some of the historical developments in the field of transitional justice since the Second World War, focusing specifically on courts. The chapter shows that, although the “toolbox” of transitional justice has been vastly expanded over the last few decades to include a wide range of institutional and non-institutional measures, claims for criminal accountability continue to constitute one of the core pillars of transitional justice when the most atrocious human rights violations are being committed. Second, the chapter offers a tentative explanation for how and why claims for criminal justice for past wrongs rarely translate into successful trials, despite the general consensus that trials are considered vital to reestablishing the rule of law, and hence contribute to transitions to peace and democracy after violent conflict. Specifically, the chapter identifies some of the obstacles that constrain judges from keeping alleged human rights perpetrators to account.