The argument is frequently made that decolonization was the rare success story of the United Nations and that the Trusteeship System and towering figures such as Ralph Bunche, did much to help accelerate or pave the way for the peaceful unfolding of this process. This chapter explores the limitations of the trusteeship system and of the impact of United Nations (UN) personnel in shaping decolonization in trust territories. It reminds us that the specific way in which decolonization unfolded, resulting in a system of independent nation-states, was no foregone conclusion at the time, and no result of the founding of the UN. The Charter gave pro- and anti-colonialists alike ammunition to argue their case: continued imperial tutelage, or a world based on self-determination. There were multiple political projects between these two poles and UN officials at the time were hoping to shape international debates and the postwar transformation of empire by setting an example with UN trust territories. However, UN influence in these territories was severely limited. Nevertheless, UN ideas about developmental statebuilding in trust territories prefigured more far-reaching experiments in “international territorial administration” that were realized in UN member states and disputed territories during the Cold War and after.