Abstract: This contribution aims at reflecting on the teaching and learning challenges faced at LUISS Business School, where Digital Design Thinking tools and techniques have been experienced both by professors in the context of the Faculty Digital Transformation program, as much as by students during the Agile Organization, UX and Digital Design Thinking courses taught in pre and post-pandemic times. Flipped learning principles, video mobile learning, and digital prototyping tools facilitated the teachers' and the students' dedicated hybrid and blended sessions. In all instances, adult learners experienced the Google Design Sprints flow, as they were guided in the debrief session to understand both what happened and what made it happen. Participating in the process - both physically and remotely - contributed to strengthening trust in the process itself. Design Thinking is all about navigating ambiguity, investigating reality, connecting dots and coming up with unexpected solutions to wicked problems. In the synchronous and asynchronous learning environments observed, the beauty of teaching and learning such a practical and theoretical subject unfolded in various levels engaged, such as creativity, empathy, heuristics, logic inductive, deductive or abductive.