This study regards the estimate of olive oil pruning biomass. The objective is to increase the knowledge of pruning biomass availability to business purposes. Having recognized the importance of both uncertainty and dynamics, we first estimate the probability distribution of the yields in a small farms sample and then determine the related expected value of pruning olive oil yield. We use these estimates to draw microscenarios illustrating the dynamics of the pruning biomass yields based on the enlargement of the number of trees per hectare (intensification) and of the olive oil crop area (specialization). The results show how intensification and specialization determine a mosaic pattern of changes in the pruning yields probabilities. The resulting estimate of the pruning biomass availability is similar to those provided in literature for the Italian case. Across the Italian regions, the difference between the expected pruning yield and a theoretical yield index decreases as the specialization increases. Two validity boundaries of the model are presented.The study concludes noting that, unless they are associated, intensification and specification not systematically augment the average olive oil pruning biomass yield in a territory and that the yields increase appears to be more probable beyond intensification large values.