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Engaging families was among the many challenges educators faced during the pandemic. While social distancing measures and school closures created physical barriers between families and schools, caregivers were asked to participate more directly in their children’s virtual learning. Engagement strategies were further tested in a context where school-community relationships have become increasingly politicized. This paper draws on a qualitative data gathered in six schools located in New York State. Interviews and focus groups with educators elucidate the challenges educators experienced engaging family members as well as the engagement strategies they utilized. Such findings are crucial to better understand the experiences of educators during the pandemic and techniques which can effectively engage families under difficult circumstances.