The goal of Cognitive Hack is to introduce readers to the evolution of emerging technologies, many in very early stage of development, being considered to address what some believe to be the weakest link in cybersecurity—the human mind. This chapter demonstrates how security is evolving and to develop a process for governance and a framework for operationalizing a cognitive risk program inclusive of advanced technologies as they emerge and practical steps for understanding risk beyond today's simplistic and qualitative approach to risk assessment. The cognitive processes involved in situational awareness are situational understanding, situational assessment, mental models, and sensemaking. Cognitive informatics is multidisciplinary in approach and is informed by research in psychology, behavioral science, neuroscience, artificial intelligence, and linguistics. Behavioral and cognitive science makes us more aware of these unconscious failings, allowing security and risk professionals to recognize the pitfalls and make corrective adjustments before communications deteriorate.