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The COVID-19 pandemic and subsequent school closures forced educators to seek new means of engaging students, especially in schools serving low-income communities hit hard by the pandemic. This exploratory virtual ethnography, part of a larger study on the culture of progressive (or student-centered) schools, follows one innovative urban high school as it shifted from in-person to remote schooling. It documents how the school attempted to use Instagram to reach students and counter the social isolation associated with the COVID-19 shutdown. We find the school used virtual spaces to enact culturally sustaining pedagogical practices in the absence of ‘real world’ interactions. The school’s Instagram emphasized positive relationships, celebrated resilience in the face of challenges, and affirmed student cultures and identities. Our data suggest that this forum played an important role in sustaining school culture and student-adult connections during an extremely challenging period for the school community.