This paper describes the method used by the Italian Classification Society RINA to develop new Rig Certification Rules. These Rules have been mostly based on failures observation, and their starting point has been a systematic study of dismastings occurred on boats of various types and sizes. Examining many of these events, typical collapse modes have been identified, and specific solutions have been proposed. Within this study a first attempt to a novel rig “dynamic” structural assessment has been developed taking advantage of a new integrated (CFD+FEM/FEA) analytical tool. Theoretical analyses have been compared with experimental data collected during extensive sailing tests on board a 94ft yacht.