It’s important to prepare students for benchmark and end-of-year assessments. Deepening their knowledge of literature and the history/culture that produced these literary texts is also necessary. Therefore, one can inform students’ understanding of literature and history by preparing them for standardized tests. Or not? Or the other way around? Catch-22 is replete with what appear to be logic games that deal with incredibly complex issues, such as war, obedience, rules and order, bureaucracy, loyalty, and patriotism. On the one hand, these logic puzzles have the potential to torment the reader. At the same time, however, the novel’s examples provide great opportunities for students to unpack and understand concepts like “doublespeak,” de jure versus de facto laws and regulations, or at least contemporary media speak (which is just as useful!).