This seminar challenges the traditional conversation about digital twins and machine learning, by proposing a different paradigm for smart cities transformation centered in new human-infrastructure interfaces. This discussion explores the area of human decisions and cognition of the built environment enabling transformations of human interacting with structures in a new environment. To date, new technologies collecting data of the built environment are cheaper, more accurate, diverse, and more accessible than ever before. However, the use and implementation of these new technologies to structural engineers to assess, inspect, or inform actions have been very limited. By empowering human-machine interfaces and fostering human involvement and participation (human-in-the-loop), this seminar will present specific practical implementations about how the collection of data, their analysis, and their interpretation can inform (and transform) human decisions. Specific applications include the connection of Augmented Reality with Wireless Sensors Networks, AI, ML, Structural Dynamics, and Inspections.