Grassland ecosystems are one of the most common land use types worldwide. The sustainability of extensive livestock production systems requires the optimization of soil management, pasture production and animal grazing. Montado is an agro-silvo-pastoral system characterized by a high complexity as a result of the interactions between climate, soil, pasture, trees and animals. It is in this highly unpredictable context that dynamic management decisions have to be made, for example with respect to soil fertilization or pH correction, grazing or animal supplementation. This study shows, through case studies, the potential of the application of Precision Agriculture (PA) strategies and technologies for monitoring indicators of the Mediterranean Montado multifunctional ecosystem, specific environmental results, namely on soil health and functionality or pasture productivity, quality, or biodiversity, in a holistic and sustainable approach. The use, calibration and validation of soil and pasture proximal sensors, animal GPS (global positioning system) receivers and satellite images opens perspectives to explore new solutions to respond to the new economic and environmental challenges and ensures the resilience of this ecosystem.