This study aims to explore the diverse reactions of farmers to two major stressors of the citrus agri-food system in the region of Ileia, in Southwestern Greece, with a special focus on farmers’ institutional affiliation with local collectivities. These stressors are the economic crisis that burst out in Greece at 2009/2010 and an insect outbreak, which has seriously damaged citrus groves in this region after 2013. The study draws on an analysis of the ways these stressors impact on the functioning of the system, as well as a thorough techno-economic analysis at the farm level, with data from a representative sample of 55 farms specializing in citrus fruit production. Both stressors have had serious impacts on the examined system. The analysis shows that although sample farmers were exposed to the stressors with a time difference of two years, they showed varying degrees of sensitivity, owing basically to the different strategies they followed. Through appropriately coordinated actions, farmers’ integration into collective structures can secure successful responses to systems’ stressors. Thus, they showed varying adaptive capacities to the stressors, attaining, at least in the case of one cooperative, to address effectively the sources of vulnerability.