Timor-Leste is a small state that finally achieved independence in 2002. It has had to re-build an entire education system from a small base largely destroyed in the independence struggle. This paper presents the issues identified in pre-independence meetings, and considers these within the framework of transition and transformation problems for a small island with a diverse population and a long history of colonisation, using Namibia as an apt example. Fifteen years later, teacher preparation both pre- and in-service is identified as a major issue in achieving educational and social goals, with language training a key factor. Enrolments have improved and gender equity is close to parity, but urban-rural differences remain. Late enrolments, drop-outs especially in the early years, and repetition are major hurdles in achieving an educated, knowledgeable and qualified population.