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 context that management decisions must be made, for example with respect to soil fertilization, grazing, or animal supplementation. In this work, the effect of the tree canopy on the spatial and temporal variability of the soil and productivity, quality, and floristic composition of the pasture was evaluated. Precision agriculture (PA) technologies for monitoring soil and pasture were also evaluated. The study was carried out between October 2015 and June 2018 in an experimental field of 2.3 ha. The results showed: (i) The positive impact of trees and animal grazing on soil fertility; (ii) the influence of inter-annual variability of precipitation on the pattern of pasture vegetative cycle; (iii) the positive effect of trees in pasture quality; (iv) the negative effect of trees in pasture productivity; (v) the role of pasture floristic composition as an indicator of soil limitations or climatic changes; (vi) the potential of technologies associated with the concept of PA as express tools to decision making support and for the optimization of the herbaceous stratum and the dynamic management of grazing in this ecosystem in a holistic and sustainable form.