For caregivers of school-age children, schooling at home was a significant stressor during the COVID-19 pandemic. Research demonstrates the emotional burden of taking on the role of teacher while trying to balance responsibilities related to work, household, and childcare. Yet little is known about the well-being of kinship caregivers during this time, although this population is at heightened risk for role stress and strain and emotional distress. This article shares the results of focus groups conducted as part of a larger qualitative study, the purpose of which was to understand the factors that influenced the well-being of kinship families during the pandemic, from the perspective of kinship caregivers and child welfare professionals. From these conversations, the challenges of remote learning emerged as a prominent theme, particularly for caregivers raising children with special healthcare needs, who comprised the majority of the sample. Given their pre-pandemic role stress and strain due to caregiving responsibilities, most caregivers struggled with managing their child’s learning, working from home, and caring for children with trauma histories, often with limited support and access to needed services. These findings suggest that this population needs support—potentially in the form of wrap-around services and/or social safety net provisions—to reduce their role stress and strain and improve well-being.