Previous studies suggest that the roots of school dropout (a) can be established early in life, (b) are likely to involve multilevel factors (home, child, classroom) operating prior to and during the elementary school years, and (c) can be identified by 3rd grade. The decision to drop out of school is thus a dynamic developmental process that can begin with disengagement in elementary school. Yet few studies have examined the multilevel factors that might contribute to children's early disengagement from school. In the present study, we examined associations between household chaos (i.e., disorganization and instability) from birth to age 5 and student (dis)engagement in third grade. We also examined positive parenting in early childhood (6-60 months) and child self-regulatory skills at kindergarten as potential mediators in this pathway. Participants were 1,097 children who participated in the Family Life Project, a longitudinal study of the development of children living in underresourced high poverty rural areas. Study questions were addressed using structural equation models. Results indicated that, even after taking into account a considerable number of covariates, early positive parenting and children's self-regulatory skills were viable process mechanisms through which early household disorganization, but not instability, was linked to student (dis)engagement in third grade. Findings are discussed with respect to the multilevel proximal forces at play in children's risk for early disengagement from school. [This article was co-authored by the Family Life Project Key Investigators.]