The description webpage for the Master of Science in Information Assurance program offered through the Iowa State University Department of Political Science states that “. . . information assurance—defined in terms of security, privacy, access, and reliability—is not simply a technical problem but also involves important societal dimensions. . .” [1] The purpose of this creative component is to accessibly demonstrate, with some levity, some of the challenges that arise when the technical and societal dimensions of information assurance, or cybersecurity, intersect. This work will explore how and why some goals of information assurance and cybersecurity are difficult to accomplish by drawing on the insights provided by organization theory. It will also use lessons from public policy theory to recommend pragmatic solutions to smooth the aforementioned intersection. More simply, this paper seeks to explain why pedestrian users in organizations make bad decisions that compromise cybersecurity, much to the annoyance of the developers and administrators who handle the cybersecurity show. It also seeks to provide some organizational policy solutions to these problems.