This lightning talk presents a course innovation that embeds a sequence of scaffolded tabletop exercises (TTXs) across an undergraduate Networking and Operating Systems Security course. TTXs are commonly used in industry and occasionally adapted for the classroom, but they are often delivered as isolated events. In this design, students participate in multiple exercises throughout the semester, with complexity and role responsibilities increasing over time. Early activities provide low-stakes exposure to the format, while later exercises introduce role differentiation, incident escalation, and planned failures. This progression is intended to help students build confidence in decision-making under uncertainty and pressure, while also developing teamwork, communication, and aspects of professional identity through role-play. During the semester, students complete exit tickets and “lessons learned” reports after each exercise and participate in debrief discussions that capture evolving strategies and reasoning. These artifacts, alongside classroom observations, provide evidence of how students experience the progression of exercises and how repeated engagement may better prepare them for workforce challenges by bridging the gap between theory and practice. By the time of the talk, a full semester of scaffolded TTXs will have been piloted, with examples of artifacts and classroom experiences available for discussion. The talk will share the design framework, preliminary observations, and plans for future research, and will invite feedback from the community on data collection strategies, measures of decision-making, and approaches for systematically studying the impact of scaffolded TTXs in computing education.