In the recent rise of digital learning, “flipped classrooms” have become a controversial subject. This new form of learning inverts the traditional conception of the classroom: instruction is transferred from the classroom to out-of-class (online) tasks such as pre-recorded lectures on the Internet, while class time is devoted to activities that put the knowledge into practice. These classrooms have been touted as learner-based and student-centered models of education. Yet there is still little evidence supporting the effectiveness of the flipped classroom at higher levels of education, especially in the humanities. Taking American studies as an example, I will examine some of the arguments in favor of this model, but also and most importantly some of the challenges facing the application of this new educational model in the humanities. In general, the main concern is that flipped classrooms may undermine student-teacher dialogue, viewing teachers as “moderators” who design learning environments geared to the students. At the same time, home-learning environments may compromise learner autonomy and limit learners’ opportunities for self-organized work and interaction with peers outside class. Ultimately, a critique of the concept of flipped classrooms is also a critique of the egalitarian aspirations of digital pedagogy in general.