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Learning at home, which is often facilitated by caregivers, became the primary learning space for children during the onset of the COVID-19 pandemic. Therefore, our project explored caregiver engagement with an education website during the pandemic. Guided by critical digital pedagogy and the theory of acceptance and use of technology, we collaborated with 15 caregivers with children aged 2–8 years from diverse demographics within Southern California. We investigated caregivers’ user experience with the website, unpacked how caregivers employed digital educational content and generated new content ideas through a co-design workshop. Findings show that collaborating with caregivers to create digital content allowed for a better understanding of their preferences, revealed unspoken caregiver needs, and fostered the collective design of desired outcomes.