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The perennial call for schools and classrooms to increase parent engagement, particularly in “high needs” or “low-performing” schools, often overlooks how educators, particularly classroom teachers, are prepared for school-family partnerships. Transformative school-family partnerships require transformative teacher educators and programs that rise to the challenge. This paper explores a series of discussions between community mentors and preservice teachers in partnership with a university-based teacher education program. Using critical race theory and border theory as an analytical framework, the author found implications for differentiation in preservice teachers’ development of a critical consciousness. Findings highlight strengths and challenges for community mentors of color engaged in intimate discussions with a predominantly white cohort of preservice teachers.