The paper contributes empirical observations on the phenomenon of “spoiling from within” a UN peace operation. The planning and the implementation of the mandate of the UN Transitional Administration in East Timor (UNTAET) was considerably hampered by individual and structural obstructions – by UN employees and from within the UN bureaucratic structure. Some of them were voluntary, some were not – but all of them prolongued the transitional process. An important mechanism for coping with these obstructions was the leadership of the mission.