Risk assessment has become an important topic influenced by emerging scenarios due to climate change and the ongoing challenges associated with territorial weaknesses. Working on risk, especially within the urban and architectural field, requires managing high level of complexity, numerous variables and data and demands to link different phenomena, in a predictive perspective, in order to obtain reliable and effective evaluations. The significant expansion of data collection and processing capabilities, made possible by digital technologies, raise issues regarding the affordability and interoperability of available data and, at the same time, it can serve as an unprecedented tool potentially capable of modifying and optimizing the proposed strategies in the field of cultural heritage. The collection of necessary information, its interdisciplinary management, and the limits imposed by multidimensional problems, raise complex methodological questions that can find a useful aid in information tools. Monitoring large-scale phenomena allows conclusions to be drawn regarding deterioration patterns and any emergency or preventive interventions that could make a difference in heritage safeguarding. The contribution fits within this scenario and presents a case study related to the managing and conservation of architecture at different scales in the northern Vesuvius area (Naples, Italy) in case of resumption of volcanic activity. The project is meant as a practice to find a way to ask more complex, answerable and operational queries concerning cultural heritage conservation issues widening the possibilities offered by the already existing and functioning systems in the field.