This chapter argues that successfully applying circularity frameworks in cultural heritage projects, especially those tied to local identity, shared history, and a sense of place, often requires ongoing monitoring of the socio-cultural environment, with particular attention to social sustainability. This is crucial for two main reasons: first, the socio-cultural context plays a significant role in shaping how adaptive reuse efforts are perceived and embraced, influencing changes both in the physical environment and within the local community’s mindset. Second, adaptive reuse projects themselves impact the socio-cultural landscape by introducing new ideas and solutions. This dynamic creates a feedback loop, which can either reinforce community cohesion and make the reuse project a success, or, conversely, result in minimal changes or even unintended negative consequences for the neighborhood.