: This paper discusses teaching the application of technical idea through non-technical discussions, especially the use of puzzles to engage students. After discussing the need for teaching students to evaluate contexts in which decisions about computer security must be made, we suggest the use of questions and scenarios drawn from political science, history, and other humanities to force students to apply or derive principles of computer security to unusual and unexpected situations. Our experience shows that students find the process enjoyable, stimulating, and effective. Key words: environment, judgment, instruction, computer security