There is growing recognition that cumulative economic risk places children at higher risk for depressed academic competencies (Crosnoe & Cooper, 2010; NCCP, 2008; Sameroff, 2000). Yet, children's temperamental regulation and the quality of the early childhood classroom environment have been associated with better academic skills. This study is an examination of prekindergarten classroom quality (instructional support, emotional support, organization) as a moderator between temperamental regulation and early math and literacy skills for children at varying levels of cumulative economic risk. The sample includes children enrolled in Head Start programs drawn from the FACES 2009 study. Three main findings emerged. First, for lower and highest risk children, more instructional support was associated with better math performance when children had high levels of temperamental regulation but poorer performance when children had low temperamental regulation. Second, among highest risk children, low instructional support was protective for math performance for children with low temperamental regulation and detrimental for those with high temperamental regulation. Third, for highest risk children, high classroom organization predicted better literacy scores for those with high temperamental regulation. Children with low temperamental regulation were expected to perform about the same, regardless of the level of classroom organization. Implications are discussed.