Olive growing represents the most emblematic agricultural production of the Mediterranean Basin. Plant protection is a key intervention without which it would be difficult to achieve high productivity in the field. Although progress, strategies, and tools have reached a noticeable technological level regarding the development of active substances, the same cannot be stated for agrochemical application equipment. In this context, this paper describes the PRIN project “Implementation of a Digital Tree to Optimize Technical and Environmental Performances of Crop Protection Equipment (IM GROOT)”, which aims to investigate the quality and sustainability of mechanical application of agrochemicals in olive orchards, considering spray distribution evenness and environmental impact. Particularly, the project focuses on the development of an innovative smart tool, a “Digital Tree,” which will allow the prediction of spray behavior under different field conditions. This requires accurate knowledge of sprayer mechanical features, their functioning and settings, field and crop characteristics, as well as climatic conditions. Once the “Digital Tree” is built, it will be possible to optimize olive plant protection for a more accurate, targeted, and sustainable agrochemical application through the appropriate choice of operational and managerial parameters, considering both technical and environmental aspects.