Drawing from their experiences teaching two different activism-focused writing courses, the authors consider the benefits, pitfalls, and potential dangers of activist writing pedagogy. Scott provides a retrospective on a rhetoric and writing course focused on the employment of digital rhetoric, while Katherine reflects on an activist-rhetoric course that culminated in the execution of an annual Take Back the Night rally. Despite the risk of “politicizing the classroom,” the authors argue that activist pedagogy, when thoughtfully implemented, can help students (no matter their political leanings) learn how to write, act, and think—necessary skills for a democratic society. Yet, while both authors support activist-focused rhetoric and writing courses, they also examine the ethical, pedagogical, occupational, and even legal issues that might arise from teaching such courses.