The conclusion of the electoral process in April 2002, paved the way for the declaration of independence of East Timor on 20 May 2002, making the tiny nation the world's newest democracy. The purpose of this study is to describe and analyse information on the education reconstruction process, and to make some recommendations about how to better promote a contextually relevant education in this fledgling democracy. This three-phase longitudinal study carried out over two years, is an enquiry into a transitional state struggling with multiple social, political, economic and educational constraints. The research used an interpretive case study approach within a qualitative framework. Multiple methods, sensitive to the context included in-depth interviews, focus group interviews, school visits, accumulation of documentary data and reflective narratives.