Within a backdrop of persistent volatility, uncertainty, complexity, and ambiguity in the world today, Defense and Security partners must rapidly confront the complex global challenges of their Future Operating Environment, presented not only by the next COVID-like infectious diseases but also those associated with artificial intelligence, quantum computing, terrorism/extremism, cyberattacks, climate change-related extremes, autonomous systems, targeted mis-/dis-/mal- information, supply chain threats to critical technologies, conflicts, as well as uncertainty of Allied Defense and Security commitments and others. Technologically complex interconnected systems that are rapidly evolving have become the norm in dealing with security threats. As a result, reactive approaches to crises/poly-crises have increasingly been proven untimely, ineffective, and more costly than anticipating and preparing the crisis before it occurs. As such, it is imperative to develop ways to far more rapidly perceive, understand, and act on the emerging future threats, using Innovation far more effectively in the process. An “Anticipatory Innovation” approach is proposed through integrating commonly used nested methodologies such as on the front end Futures Thinking (understood in this Chapter as a front-end structured and systematic way of using ideas about the future to anticipate and better prepare for change), Design Thinking on the back end (understood in this Chapter as a back-end non-linear, iterative process that project teams use to understand users, challenge assumptions, redefine problems and create innovative solutions to prototype and test), and Systems Thinking with Enterprise Architecture Framework (understood in this Chapter as a holistic way to investigate factors and interactions in a project that could contribute to a possible outcome, quite often involving Enterprise Architecture Framework.). Such an approach visually, crucially, and holistically links Who does What, Where, When, How, and Why of the entire Innovation. Further, key Lessons Learned in Defense suggest that “slow-innovation” traps to avoid include (1) extensive level of bureaucracy from tooth-to-tail of any innovation, (2) long politically stirred battles for regional economic impact, (3) innovation-unfriendly procurement/acquisition rules of engagement (between Government and Industry), and (4) lack of simple effective Innovation Governance. Countering any of the above traps would save years of delays on the path to timely uptake of the innovation.