I investigated eight preservice teachers’ understandings about culturally responsive pedagogy as they tutored children in writing from different ethnic, socioeconomic, cultural, and linguistic backgrounds in an afterschool program at a local community center. I utilized an embedded case study and chose constant comparison, within-case analysis and cross-case analysis. I recommend effective aspects of the field experience, which facilitated preservice teachers’ development of deeper understandings about culturally responsive pedagogy: one-on-one student teacher interaction and scaffolding critical reflection.