Two-thirds of households in Timor-Leste are engaged in farming, with more than a quarter of the working-age population dependent on subsistence agriculture. This large continuance of a very old form of agriculture creates an extremely challenging task for the country to make a strong and successful transition to sustainable agriculture. In this volume, Timor-Leste is unique in that it is the only country discussed that is not in the Association of Southeast Asian Nations (ASEAN), a political-economic union of the fastest growing economies in the world. Timor-Leste applied to join in March 2011 and is still waiting for a decision based on evaluations and monitoring of the country by ASEAN authorities. The subsistence nature of its agriculture and ASEAN demands to diversify away from the dominant gas-export basis of its economy is the major backdrop to this chapter’s analysis. By analyzing available documents and secondary data, this chapter focusses on the country’s ability to diversify its economy from subsistence to sustainable agriculture. The unchanging state of agriculture in the country is first examined, followed by charting past and present government policies on the economics of agriculture. Then, the difficulties in addressing a shift to sustainable agriculture are analyzed in the context of the need for infrastructure (including digitalization), climate resilience, self-sufficiency, and food security. Finally, Habermas’ societal evolution framework is applied to address this transition into the future.