On Reunion Island, a French overseas department, we study a potential synergy between a rise of food self-sufficiency and ecology at the scale of a food system transition (“Ecologization-Autonomization Transition” or ECAUT). To do so, we developed a method to identify and characterize different possible transition pathways. Firstly, we conducted semi-structured interviews with “network leaders”, coupled with questionnaires, to reveal ECAUT controversies and quantify how local stakeholders position themselves regarding these issues. Secondly, we studied some initiatives perceived as positive by each transition pathway’s promoters. Thirdly, by combining statistical clustering with discourse analysis, three transition paths were identified and described, ranging from an incremental adjustment to a more radical transformation. They are characterized by different degrees of structural modifications of the system, environmental requirements, and public interventions. The first one considers that transition requires to go further in the structuring of agri-food chains, to create economic value, employment and guarantee market share for some fresh and processed products, preserving a sugar cane ‘pivot’. The second one considers that policies must play a major role, supporting all types and sizes of farms to switch progressively towards agroecology and organic farming. The third one sees transition as a more radical process, which includes an agro-ecological, societal, planned and decentralized transformation of all the food system. Finally, we discuss how identified transition pathways can contribute to food self-sufficiency and ecology at food system scale, especially by pointing out their main assets and drawbacks, along with some economic and institutional lock-ins to be overcome.