Recent extreme weather events in the eastern American coastlines and the Caribbean highlight the impact of the interdependencies of critical infrastructure systems when exposed to weather extremes, and how those interdependencies cause failures of physical assets leading to adverse impacts on the health and socio-economic wellbeing of the communities in those regions. A recent example is the extraordinary case of the island of Puerto Rico (PR), in the direct path of Hurricane Maria, and the near total failure of lifeline infrastructures. This event also exemplifies how extreme events compound endemic physical, social and economic vulnerabilities often present in remote or isolated communities. The associated cascading impacts, prior to and after Hurricane Maria, are clear evidence of our limited knowledge and readiness to anticipate risks in these complex engineered, physical and human systems. This reveals the urgent need to develop scientific and social frameworks and methodologies by which communities can assess their existing preparedness to extreme climatic events, and through a multi-stakeholder engagement process and engineering analysis, evaluate and implement alternative measures to enhance the resiliency of such communities. Using PR as the case study, we are developing a data driven modeling framework for understanding the complex physical and social vulnerabilities, and interdependencies that resulted in near total failure of the physical systems.