The growing complexity of cities and the unprecedented pace of urbanisation create exposure and vulnerabilities to extreme events and crises that are difficult to manage and plan for as widely acknowledged by the existing literature. In this paper, three main challenges to be tackled are identified based on the selected literature according to the interpretation of the authors based on extended research in the field. Those challenges relate to the multi-risk environment characterising many contemporary cities, the need to overcome sectoral approaches towards increased alignment of emergency and spatial planning at different scales, and the opportunities that derive from integrated risk and resilience management. Such challenges are evidenced in the Pozzuoli case study, a densely inhabited municipality of the metropolitan city of Naples, placed into a volcanic caldera, that has been analysed in the light of the above challenges for an extended period of time of about fifty years. The in-depth assessment of the quality of urban development has been enabled by geospatial data management. Advanced geospatial information systems are not only instrumental in depicting the history of urban development in the period of consideration but also as an enabler to tackle the above-mentioned challenges. In fact, such systems permit a much more dynamic and updatable assessment of multirisk conditions and provide the basis for shared knowledge among the large number of stakeholders that are responsible for different sectoral and comprehensive urban and risk-related plans.