This article seeks to elucidate many of the avoidable difficulties that the United Nations (UN) face when intervening in a given conflict. The article begins with a review of the UN's capability to act, fund, cooperate, and coordinate in peacekeeping missions. The UN's capability to respond to conflict is, in theory, boundless; however, it is limited by the realities of operating within the UN's vast bureaucracy and the possibility of member states having competing national interests. The article then proceeds with an analysis of the UN involvement in Timor-Leste, focusing first on the United Nations Mission in East Timor - the referendum monitoring mission - and then covering larger operations such as the United Nations Transitional Administration in East Timor and the United Nations Mission of Support in East Timor, and finally analyzing more recent missions: the United Nations Office in Timor-Leste and the ongoing United Nations Integrated Mission in Timor-Leste. The article concludes that the UN's performance is dependent upon a steady commitment to supplying resources and the ability to properly assess and appropriately respond to specific realities within the context of a peacekeeping operation.