The first talk given as part of the Southeast Asia Seminar, St Antony's College during MT14 In 1999 Timor-Leste was given the opportunity to vote on a self-determination referendum that put an end to centuries of Portuguese colonial and Indonesian neo-colonial rule. Two and a half year later, Timor-Leste proclaimed its Independence, and set off on a road to create a modern, democratic state. Fifteen years have elapsed, and today most observers consider that Timor-Leste has been successful in upholding its own democracy and the rule of law. However, the road along which the country has travelled is full of hurdles and several challenges were met with varying degrees of success. In this talk, I shall start by assessing the odds faced by Timor-Leste in its endeavour to create a democratic state, and will then consider four areas of political relevance: the process of constitution-making; the role of elections and the behaviour of the electoral administration; the choice of the government system; and finally the much protracted decentralization reform. I will conclude with some notes on the challenges to democracy in the near future