In this essay, I outline strategies for a teaching module on corporate advertising errors, with a focus on the relationship between social media reactions, corporate apologies, and subsequent responses and long-term effects. I demonstrate how we read five key problematic advertising texts from Abercrombie & Fitch, Pepsi, H&M, Bud Light, Heineken, and Dove in consonance with one another. We then divide up into groups to track the life cycle of the corporate reaction-apology-response scenario in which there is a widespread negative reaction to an ad; the company apologizes and outlines possible steps for change; there is a social media evaluation of the apology; and, in some cases, key individuals involved in the text engage in the discussion. Students are empowered to develop expertise around one case and teach their colleagues, leading to a rich group discussion thinking about these ads together. In the final part of the essay, I briefly discuss a second class session in which we categorize the kinds of transgressions these advertisements embody, from racism to misogyny to anti-Semitism. We use these typologies to gain insight into the relationship between the kinds of errors showcased in ads and the nature of the response to them, thinking both within and across categories.