The people responsible for building the IT products and infrastructure of tomorrow – today’s students of the computing disciplines – oftentimes do not have the opportunity or proper motivation to develop cybersecurity skills meeting the needs of the job market. This paper introduces High Fidelity Live eXercises (HiFLiX) a teaching/learning activity designed to expose students to cybersecurity challenges resembling those they could face in a future work environment. We describe a HiFLiX prototype study, conducted as a collaboration between the Massachusetts Institute of Technology’s CyberSecurity@CSAIL research group and NASA’s Jet Propulsion Laboratory. Our analysis indicates that the proposed delivery method met the stipulated cybersecurity educational outcomes and increased the motivation for future cybersecurity studies in the majority of participants. Two previously unknown software flaws were also discovered.