Drawing on scholarship in Critical Pedagogy, this article speaks to the debate about pedagogical approaches within social justice education (SJE). The article addresses itself to privileged positionality within the context of university-based SJE, with a specific focus on race and whiteness. As a conceptual piece, it addresses some key considerations when working with liberatory pedagogies towards conscientising people from dominant positionalities, challenging some pedagogical assumptions that have achieved virtual common sense status. It indicates that we should reframe student resistance, cautions about uncritical use of dialogue and student experience in methodologies, and problematizes the advocacy of safety as a prerequisite for SJE. We end by outlining the reasons why firmly challenging students, though uncomfortable and controversial, may be necessary. (Contains 5 endnotes.)