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In this exploratory case study, I investigated how I supported novice, alternatively certified English as a New Language (ENL) teachers with planning for and enacting culturally responsive teaching (CRT). In addition, I explored teachers’ reflections on their experiences. As an informal teacher mentor, I implemented a teacher support system for two participating teachers that included four observation cycles (pre-observation lesson feedback, observation notes, debrief sessions) and written reflections. My findings indicate that I used several mentoring moves that prompted participants to reflect on their CRT experiences. Additionally, participants’ CRT experiences depended on their orientation toward teaching ELLs and their readiness to examine potential flaws in their thinking, lessons, or delivery.