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In this self-study, I explore the role I played in supporting teachers to confront barriers to enacting culturally responsive pedagogy (CRP). I identify the school, classroom, and identity challenges that two secondary English as New Language teachers faced, and I examine my mentoring moves. I engaged each participant in six teacher observation rounds and two semi-structured interviews. I employed multiple inductive coding rounds, the constant comparative method, and a critical friend to refine my interpretations. I discovered that I helped teachers unpack and cope with obstacles via validation, giving advice, redirection, and challenging teachers to consider bias, school context, and the student’s perspective. The implications are that mentors should help teachers discuss their contextual challenges as part of CRP support.