This chapter presents an analysis on Kofi Annan’s mediation efforts in Syria and focuses on his agency when overseeing the UN’s entry into the Syrian conflict. The chapter is divided in three main sections. The first offers a concise background of the main mediation initiatives pursued during Annan’s time as mediator. Of which there were five main mediation policies and responses – the mediator’s entry into the conflict, the Six-Point Plan, the nationwide ceasefire and deployment of UNSMIS, the Geneva I process, and the mediator’s resignation. Using a first-level analysis, the second section continues to elucidate the agency of the mediator in shaping each of these mediation outcomes. Finally, the third section explores the dynamics behind the mediator’s decision-making. Specifically, it examines how the mediator’s key strategic perceptions influenced his decision-making. Drawing on the contingency model, four categories of perceptions are studied – the identity of the mediator, the context of mediation, the parties, and the process of mediation. Building off this analysis, the chapter proposes general links between each category of perceptions and specific mediation behaviors.