The paper outlines a workflow demonstrating how digital methodologies can enhance the assessment of overturning mechanisms in historic built heritage. Using a specific case study, it is shown that digital twin models can assist with conservation and maintenance measures, such as structural assessment. This study underscores the meticulousness of the research process, particularly in the importance of digital technologies in enhancing built heritage conservation and management methods, especially for structural monitoring of historic masonry. Accurate datasets are critical since the studied architectural features are complicated and have deteriorated. Building a structural evaluation model that can capture early-stage deformations accurately involves a multidisciplinary approach that integrates historical study, visual examination, and instrumental diagnostics. Early warning indicators of damage processes may be detected by digital models before apparent fractures emerge, which is a crucial outcome of this research. Subtle deformations before collapse can be identified by examining high-resolution geometric data in conjunction with material and structural properties. It is essential to get data with a high degree of reliability since the precision of the digital model determines how accurate the structural analysis will be. As a result, the evaluation revealed the gradual activation of kinematic phenomena and highlighted important façade parts that were being overturned. These findings informed a structural intervention strategy tailored to the building’s specific conditions, ensuring that conservation decisions were data-driven and that the broader architectural design process benefitted from a structurally informed approach, improving both safety and long-term preservation strategies.