This book frames the many-sided fragilities of Hunan Province’s Heritage. It originates from a ten-year-long international cooperation between Politecnico di Milano (Italy), dealing from the Seventies with architectural preservation and adaptive reuse’s teaching and research activities, and the School of Architecture of the Hunan University of Changsha (China). From the Preservation of Landscape Heritage to Historical cities and settlements preservation and ancient and modern architecture preservation, the tangible and intangible cultural heritage protection and valorization, from the social repercussions to the environmental issues, the contributions introduce different aspects of Hunan territory’s cultural richness and fragility. The common aim of the rich mosaic of case studies presented at different scales is mapping, understanding, and considering the weaknesses of sites to be addressed sustainably. This is done while seeking cultural resilience-driven preservation solutions regarding operational guidelines and policies, risk assessment, social awareness, and teaching innovation. There is also a focus on virtuous multi-scale management of advanced digital technologies used to describe the current conditions and to drive the compatible design methodology on cultural heritage.