As new communication technologies enter the classroom, teachers must attend to how digital platforms impact the interpersonal practices of teaching and learning. In this article, I study email exchanges with three of my students--Jorge, Adriana, and Jason--over the course of one year in an 11th-grade English class at River High School, a struggling American school subject to intervention for failing to meet the federal No Child Left Behind requirements. I ask several questions: what role does email play in my relationships with students; what does email reveal about the ideological content of my communication with students; and how could I use email transformatively? When I studied these email exchanges, I found that while email has the potential to transform literacy instruction, it can also perpetuate a poor student/teacher relationship and reproduce neoliberal narratives that narrowly imagine students as test-takers, workers, and consumers.