Agri-food social-ecological systems (AFSES) embrace complex interactions and processes of food production, processing, and commercialization that are subject to constant changes. This study develops a heuristic approach using the adaptive cycle (AC) and a transformation potential measure to identify the historical trajectory of a coffee AFSES at a watershed scale in Copalita, Mexico, over 40 years from 1980 to 2020. Primary information was collected through semistructured interviews. The results show that the system interactions depend on economic, social, and environmental stressors and shocks affecting different temporal and spatial scales. The cumulative effects of driving forces and adaptive strategies have influenced the system to not complete the AC phases. Additionally, the results show that some adaptive strategies can become new stressors with time. Driving forces, adaptive strategies, tipping points, trade-offs and interactions within the AFSES could be identified as the main aspects defining system resilience.