According to a 2018 survey conducted by The Conference on Jewish Material Claims Against Germany, "over one-fifth of Millennials (22%) haven't heard or are not sure if they have heard of the Holocaust." Since the publication of that study, calls for Holocaust-mandated education have been intensifying. Some academics and teachers have advocated the use of simulations to create empathy for Holocaust victims and survivors. However, sensitive subjects such as the Holocaust must be taught with great care, keeping sound, age-appropriate pedagogical goals in mind. Otherwise, it may do more harm than good. This article discusses two early twenty-first-century Holocaust-themed short stories which serve as stern warnings about the potential dangers and lasting effects of irresponsible Holocaust pedagogy. In Ellen Umansky's "How to Make it to the Promised Land" (2003) and Nathan Englander's "What We Talk About When We Talk About Anne Frank" (2013), characters engage in "what if" scenarios by playing seemingly harmless Holocaust "games" that take a dark turn and conclude with unsettling revelations. While the stories are works of fiction, the analog "games" described in both narratives are loose adaptations of actual games hat Umansky and Englander played as teens.