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This chapter examines the contradictions between the United Nations's essential humanitarian role in advocating for Palestinians and its failure in the more political process of ensuring their self-determination. The issue of refugees from Palestine has been a compelling political and humanitarian crisis since 1948. In the 1948 Arab-Israeli War, about 750,000 Palestinians either fled or were forced to flee from their homes in what would become the state of Israel. UNRWA was created by the UN General Assembly in 1949 to address the needs of the Palestinian refugees until a political solution to their plight could be found. Drawing on experience as a former commissioner-general of the United Nations Relief and Works Agency (UNRWA) and the current United Nations High Commissioner for Refugees (UNHCR), the chapter reflects on the everyday struggles and resilience of Palestinian refugees and explains why leading UNRWA is one of the UN's most challenging managerial tasks.