Purpose: This article explores how pandemic-induced instructional changes and remote learning, in particular, affected teachers' relational work with students. Research Methods/Approach: It draws on semistructured interviews with 33 teachers and three instructional coaches across three secondary schools in one urban district. Interviews were conducted remotely over two school years (2020-21, 2021-22). Findings: Teachers' changing instructional conditions dramatically limited their relational work with students and tended to negatively affect their sense of success and overall satisfaction. Teachers found various ways to cope, but most experienced loss and diminished commitment as teaching grew unfamiliar and teacher-student interactions grew complicated. As participants became estranged from students, they also became estranged from teaching more generally. Many increasingly questioned their careers, and some left their positions. Implications: These findings offer a needed, detailed view of teachers' everyday work during the pandemic. They raise implications for districts continuing to reorient teaching and learning after COVID-19 and urge policy makers and school leaders to respond to teachers' and students' relational losses after a period of disrupted schooling. They showcase teacher-student relations' contextualized nature, an underexamined area. Finally, they advance conceptual understanding of teacher-student relationships, introducing the concept of "estrangement" to explain the consequences of instructional contexts that create social distance between teachers and students.