In this presentation I outline how the pedagogy of illustration history has changed since I began teaching it in 2009. I discuss the origin and traditional content of such courses in the US and Canada, the strengths and weaknesses of those inherited approaches, and how I have tried to address evolving needs over the years in response to demands for greater diversity, accommodations of learning styles and disabilities, online pandemic delivery, and in 2023, academically underprepared and relatively less socialized students. I review the use of the 2018 History of Illustration textbook that I coedited with Susan Doyle and Whitney Sherman, as well as material I have supplemented the textbook with; and critically discuss some of the active learning exercises and assignments that I have introduced as I have attempted to move away from lecture and exam-based modes. In sum, I interrogate traditional pedagogy and suggest alternatives.