Between the beginning of the external intervention in Timor-Leste in September 1999 and the national crisis of 2006, the country was considered one of the most successful cases of external promotion of democracy and nation-state building. The conditions were about as ideal as they could be: there had been a general consensus over the future between external and internal actors, an almost complete lack of spoilers, and a high degree of international interest. Nonetheless, the result to date has been an imperfect democracy, illustrated by a lack of socio-economic progress, a politicization of the security forces, corruption, and a poorly functioning judiciary. While some have blamed external actors for imposing their ”kingdom” in Timor-Leste and others see the main problems in the East Timorese political culture, this essay will argue that the situation is a more complex mix of internal and external factors. Building a democratic nation-state is a challenging exercise, even given the most ideal of circumstances.