Role-playing games offer powerful opportunities for players to engage with history, such as allowing players to fictionally situate themselves in a historical period. When it comes to the Holocaust, however, games face serious issues such as the potential trivialization of the Holocaust or players learning to blame the victims. In this design case, we show one way that these issues can be addressed through game design techniques. We bring together the literature on games and Holocaust education to define a set of design challenges for Holocaust-related historical role-playing games; we describe "Rosenstrasse," a role-playing game in which players adopt the roles of Jewish and non-Jewish Germans in mixed marriages in Berlin between 1933 and 1943; and we illustrate specific game design decisions within "Rosenstrasse" that address the challenges identified in this paper. This work aims to help other designers address the same set of challenges in their own game design process.