The Italian school infrastructure has suffered in recent decades from an immobility that has generated critical issues and shortcomings in the management of structures, safety adjustments, and innovations in the architectural and pedagogical model. This type of stasis, due to the scarcity of resources on a national scale and the decrease in the birth rate of the country, has meant that the buildings are largely inadequate from both a regulatory and socio/pedagogical point of view, with a level of degradation that is leading to a progressive abandonment of several structures, generating further insecurity at the urban level. In Italy, the current health emergency (SARS-CoV-2), with the necessity of wider spaces for social distancing and less numerous classes, has further highlighted the strongly problematic nature of an extensive and often obsolete school building heritage, raising the need to reevaluate heritage in terms of safety, accessibility, economic impact, and, last but not least, social cohesion. The paper proposes an approach that starts from the analysis of regulations and data on a national scale related to the structural and formal conditions of school buildings, interpreting and evaluating their safety with a holistic approach, to then proceed to the definition of a design survey matrix able to classify the selected cases and give an interpretative reading that includes the vastest number of characterizing factors. The Italian territory (between Abruzzo, Lazio, and Umbria) affected by the 2016 and 2017 earthquakes has been selected as a significant case study due to its obvious conditions of further criticality for the formulation of an evaluation methodology through an extensive field survey, cross-referenced with available data on the resilience of school structures and their role in the urban fabric, with the ultimate aim of identifying functional methods for their adaptation to a contemporary, safe, flexible, and shared school model with local communities.