The underlying premise of the Millennial Cybersecurity Project is that the best way to communicate with millennials is through the language of technology. Most organizations today employ communications strategies that are better suited to previous generations. Instead of more traditional text-based materials and face-to-face interactions, this project demonstrates that risky behaviors can be reduced by moving from more traditional approaches to digitally-mediated and interactive online approaches that are more aligned with millennial familiarity and comfort with ” messaging ” that is short and simple—and supported by graphics and symbols for fast and easy comprehension. In particular we demonstrate the effectiveness of 1) the use of real-time feedback of (lack of) conformance with security best practices, 2) the online reinforcement of best practices by encoding them in a ” strategy ” that is delivered digitally, and 3) the use of avatars or other digital (self) representations to personalize the messaging. While stereotypes portray millennials as risk-seeking and blithely unaware of threats to and policies regarding cybersecurity, our results reveal a broad range of attitudes from highly aware and competent to completely uninformed and dangerous.