This longitudinal study examined the relations between multiple risk indexes representing contextual adversity, income-to-needs ratios, and the elementary school adjustment of children from economically disadvantaged families. The results provide evidence for volatility in family circumstances over 2-year intervals from preschool to 5th grade, for relations between the contextual risk indexes and change in externalizing behavior, and for relations between the income-to-needs ratios and change in academic competence. The results also show differences in the timing of the effects. Little evidence was found for persistence effects. Theoretical implications concern conceptualizations of the diverse and dynamic nature of the family circumstances experienced by disadvantaged children.