This chapter offers my reflections on the challenges of teaching courses on dynamic and difficult topics. As a case, I explore the challenges specific to my upper-level undergraduate seminar titled, “Problems in Political Science: Disaster Politics” as I taught it during the novel coronavirus outbreak (Covid-19) in the summer of 2020. The course is built upon the idea that disasters offer analytical windows through which we are better able to observe the ways in which institutions and incentives affect politics. While the context of this is quite specific—the politics of disasters—my hope is that these musings are useful for anyone teaching or preparing to teach courses on dynamic, difficult, and/or sensitive topics.