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Providing meaningful feedback to student writers is a nuanced, fully human endeavor. Thus, teaching preservice teachers, in all disciplines, to respond to students’ writing is a complex task, one that requires intentional instruction and practice. In this article, we use practitioner inquiry to analyze our experiences and teaching approaches with preservice teachers who provided feedback to middle school writers through three public school partnerships. The partnerships employed varied modes of communication, including digital platforms, paper notebooks, letter writing, one-to-one tutoring, and face-to-face school visits. Response patterns suggest authentic experiences that explicitly teach and support writing practice spur the ability of preservice teachers in crafting relational, generative feedback to student writers while considering the affective experience.