A comprehensive understanding of the flood risks posed by various present and future scenarios is particularly crucial for university campuses in flood-prone areas. Accurately modeling and predicting flood impacts at the scale of individual buildings has become increasingly essential to formulating effective mitigation strategies. However, most flood modeling techniques treat buildings as solid, non-porous blocks, which overlooks the existence of various fenestrations such as doors, windows, and ventilators near the ground level. This limitation hampers the accuracy of flood scenario analyses since these fenestrations can potentially allow floodwaters to enter the buildings. As part of MIT’s commitment to building a resilient and adapted campus in the face of a changing climate, the Office of Sustainability and the Urban Risk Lab at MIT designed a crowd-mapping software system and involved student volunteers on the MIT campus to precisely map the locations, sizes, and conditions of building porosities. The research presented in this chapter aims to enhance the accuracy of flood risk assessments on campuses characterized by large assemblages of interconnected buildings by introducing a novel approach to collect and harness data on surface-level building openings as a variable in flood modeling. This approach facilitates a finer estimation/more precise simulation of floodwater movement traversing through the campus’s ground floor and subterranean passages. By utilizing the campus as a living laboratory, the project not only enhances technical flood modeling but also fosters community awareness and engagement in flood resilience efforts.