Forests are intrinsically coupled to human dynamics, both temporally and spatially. This evolution is conditioned by global changes in climatic conditions (teleconnections) and distant socio-economical processes (telecoupling). The main goal of this study is to describe the teleconnections and telecoupling dynamics that have shaped structure and processes in a dry-edge—highly vulnerable to desertification—Mediterranean pine forest during the last century and to evaluate the contribution of historical management strategies to this coupled human and natural system’s (CHANS) overall resilience. For this study, we collected relevant human and natural system data from a dry edge Pinus pinaster Ait. located forest in Central Spain using a CHANS analytical framework operationalizing telecoupling and teleconnection. A key extractive economic activity in the studied forest was resin tapping, which was the main form of land use from the 1920s to the 1950s. Since the 1950s changes in the Spanish economy linked to the emergence of new resin-producing countries, such as China, led to a sharp decline in resin production. Despite additional human system transformations affecting forest governance (e.g., the Spanish Civil War, the transition to democracy, European integration, etc.) and changes in biophysical conditions linked to climate change (e.g., aridification, CO₂ fertilization), the standing stocks of P. pinaster increased during the monitoring period due to sound technical and management planning bolstering overall resilience. These historical management decisions, we argue, successfully reconciled overall resilience goals (defined as the maintenance of forest function beyond and desertification avoidance) with three successive historical forest use challenges: intensive firewood collection by local communities in fragile sandy soils, extensive pastoralism in the forest understory and tradeoffs between resin tapping damaged trees, timber production and tree cover as well as the emerging risks of wildfire and climate change.