The adaptability of olive-growing systems to climate change is studied in the Sierra Mágina region (Andalusia) using an interdisciplinary approach that evaluates and makes associations across climate, water resources, and socioeconomic strategies. First, the evolution of rainfall and temperature during the twenty-first century is assessed at the local scale using 17 regional climate model (RCM) simulations. A 15%–30% rainfall reduction is expected in the fall combined with a 7%–9% annual reduction by 2030–50. Based on a regression model relating yields to rainfall, residual yields (independent of the increasing trend in the present period and from the biennial fruit bearing of the olive tree) are projected to decrease by 7% and 3.5% by 2030–50 for rainfed and irrigated olive groves, respectively. Substantial uncertainties in these results are discussed. A GIS analysis shows a reduction of ground and surface water resources, which are the basis of the present adaptation to rainfall variability, and an uneven potential for adaptation to climate change in the Sierra Mágina region. Despite the important challenges faced by this rural region, there is no consensus among the local key actors regarding adaptation strategies. This is due in part to the diversity among farmers, but also to the different levels of awareness about climate change among all the stakeholders and farmers. Since the projected decline in medium-range future yields is not very high, there might be time and possibilities, especially in the northern part of the Sierra Mágina, to build a local adaptability strategy within the next 20 years that would take into account improved methods of water management and a better economic valorization of olive oil. But at longer time scales, the adaptability of the olive-growing system to yield and water resource declines seems to be threatened.