The study examines the methodologies for the valorization and conservation through innovative design strategies aimed at the typological and functional transformation and metamorphosis of the monumental heritage. The study examines the cultural and scientific framework dealing with the technological, sustainable and functional regeneration aimed at the preservation of the monumental heritage of contemporary architecture: the study, focused on the paradigm of the Interpretation, proposes the procedures of scientific analysis, innovative and experimental strategies for the redevelopment of monumental buildings (according to the meaning of iconic and complex infra/megastructure architectures). The Interpretation paradigm is achieved to detect the technological resilience forms capable of activating performances of absorption and reaction towards the perturbative pressures caused by the multidimensional vulnerability and obsolescence phenomena. The theoretical and operational approach proposes the strategies directed at: the selective and mediation methodologies to metabolize and mitigate the physical and techno-economic stress conditions; the environmental (eco-efficient) re/balancing and the proceeding of the ongoing functionality and activities, according to potentially replicable and generalizable Interpretation and executive feasibility methods. The thesis and proposals, put forward on both sustainable and adaptive regeneration and advenience resilience, are demonstrated through the experimental, modelling and design simulation applied to the Kansai International Airport Terminal in Osaka.