Parents are increasingly choosing to enroll their students in online schools rather than traditional brick-and-mortar schools. Despite the growth of online schooling, however, there is extremely limited research on such schooling and the role parents play in the educational outcomes of students enrolled in online schools. The current quantitative, survey-based study, guided by an expectancy-value-cost theoretical framework, attempts to determine factors relating to parental motivation in helping their online students, and how parental motivation impacts student learning. Participants were drawn from a snowball sample of parents on social media, as well as compensated participants drawn from Mechanical Turk, whose children were enrolled in online schools any time from fall 2019 through spring 2022. Path analysis revealed that parents’ online self-efficacy predicted lower parent perceived cost and higher expectancy for success in helping with children’s online elementary school education. Lower cost and higher expectancy for success in turn predicted higher parental perceptions of their student’s learning. Teacher support did not predict parent motivation, but the framing of survey questions involving teacher support likely did not fully capture the impact of teacher support on parent motivation. Implications for practice include bolstering parents online self-efficacy in order to reduce perceived costs and improve expectancy for success.