Authentication of authenticity is an evolving, less-researched field of inquiry in heritage tourism. This book advances research on this subject by exploring different authentication processes and scrutinizes their resilience in building transformative heritage tourism pathways. It offers a kaleidoscopic view of the manner authenticity has evolved over the last several decades by observing a broad spectrum of cultural expressions. The evolution and meaningfulness of negotiated authenticity is identified and discussed in the context of pre-, intra- and post-pandemic times. This book focuses on the moral and existentialist trajectories or authenticity and the notion of self-authentication. It proposes a smart resilient authentication model to delicately negotiate the objective and self-dimensions of authenticity in transformative times. Furthermore, by sharing examples of best practices, it offers unique insights on how authenticity is authenticated and mediated via digital platforms and artificial intelligence. This book offers novel perspectives on negotiated authenticity and its authentication in heritage tourism and will appeal to both practitioners and students/scholars in Heritage studies; Design and Innovation; Tourism Studies; Geography and Planning across North America, Europe, and East-Asian countries.