Numerous positive child outcomes are associated with parental involvement in their child's school, but the longitudinal impact of parenting stress and parent-child engagement on parental school involvement remains less understood. Using data from the Fragile Families and Child Wellbeing Study (N = 528), this study examined the impact of single mothers' parenting stress at child age three and parental engagement at child age five on parental home-based school involvement at child age nine. Analyses were based on structural equation modeling that tested direct and indirect effects. Higher levels of single mothers' parenting stress lowered parental engagement at age five, and higher levels of parental engagement at child age five increased home-based school involvement at child age nine. Tests of indirect effects confirmed that parental engagement mediated the relation between parenting stress and home-based school involvement.