Teacher learning is a complex and important idea, given the proposed centralized role these individuals have in eradicating the inequitable school outcomes for students of color. It is necessary that researchers document the complex trajectory of learning that occurs as teachers engage in critical reflection on their practice. In the current study, white, female teachers examined the ways their own beliefs, assumptions, and values impacted classroom interactions with students of color, as well as the ways power, privilege, and whiteness manifested in the classroom. Utilizing Cultural Historical Activity Theory (CHAT) as a framework for understanding teacher learning as product and process, as well as whiteness and feminist theories as interrogative tools, the complex and iterative learning trajectories of two elementary school teachers are described in detail. The participating teachers engaged in critical reflection in the context of collaborative interviews, in which they reflected upon excerpts from classroom videos using the lenses of whiteness, power, and privilege in order to consider their own and others' teaching related to deeply held beliefs, assumptions, and values.