Collapse of electric and water infrastructure throughout Puerto Rico with Hurricane Maria is well documented but assessment of interactions among environment, infrastructure, and society is lacking. A classification system is developed to assess the resilience of each component based on principles of ecosystem responses to long-term and unexpected environmental change. All infrastructure sectors have experienced long-term decline because of a patch and stabilize approach that excludes strengthen and innovate. Maria was the tipping point for system collapse. The weakest sector, however, is governance and an inability to change direction from traditional centralized, engineered approaches incapable of meeting current or projected changes in resource availability and societal needs. The two most resilient sectors are environment and human communities. Their strong interrelationship is key to developing decentralized, nature-based solutions to address immediate and projected threats to resiliency and sustainability of communities in Puerto Rico. Still in its infancy, community ownership of the water-energy-food Nexus shows a great promise for island.