In Timor-Leste, rice is a source of livehood and a staple food. However, it presents persistently low yield, quality, price, and value to consumers, which, allied with climate projections and pressure for higher quality and productivity, raised logistics costs, and subsidized imports, creates a need to identify drivers/inhibitors of sustainable development. This chapter investigates rice agri-food chain sustainable development by recording the main actors involved and understanding their perspectives. Interviews, questionnaires, observation, and focus group have been applied to understand how sustainable development can be triggered. Results show that actors are not accurately coordinated to find a future sustainable development. An alignment of activities, innovation, best practices, and cooperation are recommended towards a future sustainability plan as a starting point to agrifood rice development. Each element of this development should be measured and quantified in future research.