Umbrella pine (Pinus pinea L.) cones take three years to develop. With the increasing frequency of extreme droughts, water available for trees has decreased—climate change is a reality. The cone’s survival in its first two years of development and the average cone weight during its last year of maturation is affected, thus, reducing kernel quantity and quality. Climate change has resulted in forest fires becoming an inescapable issue in forest management planning. A literature review was carried out, focusing, on one hand, the predicted climatic changes for the Mediterranean basin and, on the other hand, the umbrella pine silvicultural mechanisms at tree, stand, and landscape levels that may help to face these constraints. Finally, the Portuguese case was focused, describing the management practices that are being adopted to achieve, even when the period of cone formation and growth include dry years, one to six tons of cones per hectare per year in adult stands.