In the effort to "flatten the curve" of the COVID-19 pandemic, teachers were required to adapt their curricula, pedagogy, and relationships with their students to remote learning structures. In the traditional classroom context, teachers have a number of ways to check in on and connect with their students that do not translate to the virtual classroom. Using data gathered through an online qualitative survey of over 800 Chicago teachers in July 2020, this article will examine the ways that the shift to remote learning challenged teachers' relationships with their students during the spring of 2020. By utilizing social presence theory and considering the significance of emotional connection in teacher-student relationships, the study captures some of the relational challenges that teachers experienced during the initial months of remote instruction. The study identifies increased individualization, deeper holistic understandings of students, and a diversity of mechanisms of engagement as pedagogical techniques that allowed teachers to maintain and even improve their relationships with students.