Wrestling with issues of racism and colonization in the classroom requires significant nuance from dominantly positioned educators. In this article, we weave together a narrative unpacking of an uncomfortable experience in a graduate level class with an exploration of relevant theoretical literature. Our reflection on practice takes up the possibilities for anti-oppressive education to engage with the partial knowledge of educators and students. Ultimately, engaging in a pedagogy of discomfort is necessary to unsettle dominantly positioned educators and students and enable a move towards bearing witness to the unequal realities of Canadian society. In order to begin to enter more deeply into relationships of accountability between non-Indigenous and Indigenous peoples, teaching moments such as these are inevitable, if not required.