Cuba's transition to agroecology is perhaps as widely known as it is misunderstood. In response to the economic crisis of the early 1990s, the Cuban agricultural sector largely departed from the industrial model of food production that it had previously pursued. The subsequent transition towards an agroecological model has been a dynamic and uneven process, elevating Cuba on the world stage as a global leader in sustainable agriculture while at the same time producing unique challenges for Cuban farmers, policy makers, researchers and academics. This article synthesizes and updates contemporary literature on the Cuban agricultural system, paying attention to both successes and shortcomings of agroecology in Cuba to date. In particular, it situates these literatures alongside contributions from academics and practitioners alike, bringing a number of data sets, experiences, and perspectives into conversation in the context of changing realities within Cuba and the nation's evolving geopolitical relationship with the United States. By analyzing both the historical and contemporary processes through which agroecology has taken root in Cuba, we demonstrate that, despite its uneven and incomplete implementation, such a sustainable agroecological transition holds great, untapped potential. Agroecology in Cuba currently faces pressure from normalizing Cuba-US relations, with potentially profound implications for agriculture in both countries. But increasing opportunities are also emerging for investment, collaboration, knowledge exchange, and solidarity. In this paper, we provide an overview of the evolution of the Cuban agroecology movement; analyze the state of food security and challenges to food sovereignty on the island today; outline US-Cuba policy changes occurring since December 2014 that may affect the agrifood sector; and conclude with recommendations for supporting agroecology -for food security, food sovereignty, and sustainability -under this new and evolving relationship. Please refer to Supplementary Materials, DOI: https://doi.org/10.1525/elementa.337.s1, for a full text Spanish version of this article.La transición agroecológica cubana es quizás tan ampliamente conocida como malentendida. Como respuesta a la crisis económica a principio de los 90, el sector agropecuario cubano se apartó en gran medida del modelo industrial de producción alimentaria que anteriormente había perseguido. La transición posterior hacia un modelo agroecológico ha sido un proceso dinámico y heterogéneo, que 1) ha convertido a Cuba en líder en el desarrollo de una agricultura sostenible a escala global y que, al mismo tiempo, 2) ha producido