Given the nature of their responsibilities in field-based settings, university supervisors play an important role in preparing pre-service teachers to become culturally responsive and critically reflective special educators. However, supervisors themselves may not have the experience and training necessary to do so, and limited guidance is available regarding effective mentorship practices to foster implementation of culturally and linguistically responsive pedagogy (CLRP) and critical reflection. This exploratory qualitative study examined how three supervisors engaged in post-observation conferences with their student teachers to promote critical reflection about CLRP using content and discourses analyses. Findings indicated that, although student teachers engaged in discussions about CLRP and were able to critically self-reflect, supervisors were unable to facilitate critical reflection vis-à-vis institutional practices and systemic bias. Theoretical and practical implications for supervision of practicum experiences in pre-service teacher education programs are offered.