The chapter is set out as follows. The first section examines the nature and role of the rule of law in transitional contexts and challenges to the rule of law in transitional societies. The next section discusses the work of Ruti Teitel on the rule of law dilemma. Teitel provides a useful framework for evaluating the challenges that the rule of law faces in transitional societies. The third section analyses the German and Nigerian experiences of post-authoritarian transitions from communist rule and almost three decades of military rule, respectively, providing contextual reference points for the issue. The fourth section provides a detailed discussion of the justice versus peace debate, which has been ubiquitous in transitional justice. The peace versus justice debate is poignantly captured by the South African truth and reconciliation process and the grant of amnesty for truth that was contested.