Student teaching supervisors can play an integral role in teacher candidates' ability to understand and enact culturally responsive pedagogy (CRP). However, supervisors may lack the awareness, knowledge, skill, or willingness to serve as culturally responsive supervisors. This paper reports the findings from a qualitative study to find out how supervisors described and supported CRP. We found that supervisors hold unsophisticated views of CRP and face the following challenges enacting culturally responsive supervision: feelings of inadequacy, difficulty talking about race, color-blind orientations, and a tendency to purposefully avoid race talk. We provide recommendations for professional development to address these challenges and narrow the theory-to-practice divide in order to promote the democratic education ideals of equality and justice in our schools.