This paper examines the relationship between agroecological scaling and the agrarian question, based on Puerto Rico’s contradictory agricultural and demographic tendencies in the aftermath of Hurricanes Irma and Maria. We find that labor-based intensification, literally rebuilding and recovering the diversity of farms devastated by the hurricanes, is a necessary step toward scaling out agroecology in Puerto Rico. The rebuilding of farms requires both ample manual labor and accumulated local knowledge, two elements which are difficult to bring together in Puerto Rico due to a complex interplay of historical and social factors. Decades of public policy based on the belief that the small farmer is not essential to Puerto Rico have produced a series of obstacles for farmers who wish to recover their farms. The peasant economy, a field of study that recognizes peasant farmers as capable subjects of their own historical resistance – within and against economies of empire – can be a powerful tool in the effort to recover local food systems and (re)create a vibrant small farmer sector. Here, we explore peasant balances, a capacity to aggregate daily farm management decisions into coherent, multifunctional economic strategies that allow for dynamic responses to changing environmental, social and market conditions, and how these balances relate to Puerto Rican coffee farmers’ capacity to stay on the land and transition toward agroecological production. Fieldwork included qualitative interviews with leaders of small farmers’ organizations, Puerto Rican government officials and farmers in the mountainous central region between August 2017 and March 2018.