We have a substantial appreciation of “understanding, " in the sense that we have methods and tools to help us take collected information and derive synthesized insights for a specific purpose. However, we still have a long way to go in representation, synthesis, and presentation of human qualities, unknowns, and their nonergodic futures. Military and intelligence systems are a useful example domain, in part because their problems are crisply identifiable. Usually, examinations of such systems focus on what works, but in our research, we also model what does not work, what is not modeled, and why. This chapter reviews the existing, critical edge-cases that compromised systems to the extent of being untrustworthy and putting nations and their people at risk. While the examples are from the military, we believe the analyses, partial mitigation, and research agenda are widely applicable to other domains, including shared contexts.