A decade after achieving independence, the Democratic Republic of Timor-Leste (DRTL) continues to rely upon the United Nations (UN) directly and indirectly to carry out functions typically ascribed to the state. This dependency raises the specter of what scholars concerned with the breadth and extent of recent and ongoing UN operations in places such as Timor-Leste have dubbed “neo-trusteeship.” This research advances an empirical accounting of, and explanation for, the emergence and persistence of neo-trusteeship in Timor-Leste. Careful scrutiny of the UN involvement in Timor-Leste betrays the origins and sources of the neo-trusteeship arrangement and suggests that neo-trusteeship is better understood as a by-product of the disjuncture between mandate overreach and organizational incapacity playing out within complex post-conflict environments rather than any intentional manifestation of “post-modern imperialism.”