Although critical pedagogy has been discussed in the Teaching Sociology literature for nearly twenty years, dialogues about the difficulties in practicing and implementing critical pedagogical strategies in everyday classroom life are less common. In this note, we discuss a predominant theme of our workshop: challenges and concerns that may arise when one attempts to do critical pedagogy. We focus on both challenges and potential solutions for learners, instructors, and institutions of higher education. Understanding what some of these obstacles are and how they manifest in institutions of higher learning goes a long way in devising strategies to assuage their deleterious effects.