Tree recruitment is a key process underlying stand dynamics and sustainability in managed forests. Woody plant cover is known to affect the regeneration success of Pinus nigra, suggesting the existence of facilitative plant-plant interactions. The regeneration patterns of this Mediterranean pine were analyzed across its distribution area, using data from 3226 plots of the Spanish National Forest Inventory. We aimed to test the hypothesis that seedlings establishment occurs under higher values of either canopy or shrub cover in the driest populations, as predicted by the stress-gradient hypothesis. Data were analyzed by means of Generalized Linear Models and multivariate methods. Results revealed that regeneration failure occurs on a regional scale, and that regeneration is facilitated by tree canopy cover of 55%–80%. A non-linear pattern of interaction along an aridity gradient was identified, with competition at the wettest site, high facilitation at the mid-dry sites, and low facilitation at the driest site. Evidence suggests that some shrub species may facilitate recruitment in the harsher areas. Collectively, our results reduce the possibilities of adapting forest management to drying climates by the application of alternative silvicultural prescriptions involving canopy cover.