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The COVID-19 pandemic upended the lives of families with young children as school closures and social distancing requirements left caregivers struggling to facilitate educational experiences, maintain social connections, and ensure financial stability. Considering families' increased reliance on technology to survive, this research documents parents' lived experiences adapting to technology's outsized role alongside other shifts in family life associated with the COVID-19 pandemic. In this paper, we describe a 10-week study with 30 enrolled families with children aged 3 to 13 in the United States using the asynchronous remote communities (ARC) methodology to 1) understand the benefits and challenges faced by families as they adapted technology at home to navigate the pandemic, and 2) to ideate improvements to those experiences through co-design. We found that amidst gaps in infrastructural support from schools, workplaces, and communities, parents experienced deep anxiety and took on new roles, including tech support, school administrator, and curator of meaningful activities for their children. As parents shared bold and creative technology-based solutions for improving family well-being, schooling experiences, social life, and beyond, they demonstrated their capacity to contribute to new models of learning and family life. Our findings are a call to action for CSCW researchers, designers, and family-focused practitioners to work with learning communities that incorporate parent, teacher, and technology experiences in their academic and community planning.