This book investigates how digital transformation and technological innovations are challenging traditional design paradigms and redefining the conception of interfaces, suggesting a future where interfaces seamlessly integrate into or disappear within smart objects. Through the lens of Thingk, a university spin-off of the Politecnico di Milano, it addresses the practical application of theoretical design research in creating objects that, while analog in appearance, are technologically augmented, embracing a multidisciplinary approach that includes product design, communication, and interaction design. Covering an eight-year span of experimental design and analysis, it dives into how smart objects leverage context-awareness and situated meanings, engaging users from research and co-creation to validation. The significance of this book lies in its comprehensive analysis and insights into the design process behind such objects, underscoring the need for thorough examination of how semantic reconfigurations impact on affordances and agency. With a strong emphasis on a research-through-design approach and case studies, it bridges theoretical inquiry with practical applications, offering insights into the potentials of design-driven innovation in evolving user experiences.