While there is a body of literature that considers the theory of critical pedagogy, there is significantly less literature that specifically addresses the ways in which professors attempt to apply this theory in practice. This study explored the successes and challenges that 17 self-identified critical pedagogues encounter as they endeavour to turn the theories of critical pedagogy into post-secondary classroom practices. The key research queries included: 1) what are some of the ways in which professors who espouse critical pedagogy practice it within the classroom?; and 2) what are some of the successes and challenges that critical pedagogues experience as they engage in forms of critical classroom praxis? The study results indicated the following: 1) there exists a need for ongoing articulation of critical classroom practices and how to implement these within the post-secondary classroom despite some of the challenges; 2)some of the specific claims regarding participants success with critical praxis require further critical interrogation; and 3) approaches to research about/in/for critical pedagogy need to be troubled and complicated.