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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 communities hit hardest by the pandemic. This virtual ethnography, part of larger study of the culture of progressive (or student-centered) schools, followed one innovative urban high school as it shifted from in-person to remote schooling. It documents how the school attempted to use Instagram to maintain student engagement and extend school culture to virtual spaces. We find the school successfully enacted culturally sustaining school practices in the absence of “real world” interactions. However, student engagement and response varied significantly. We argue effective social media use requires skillful moderation, evolving engagement strategies, and fluency in youth and community culture.