The ecology of economic disadvantage includes chaotic living conditions that may disrupt children's regulatory functioning and undermine mastery oriented responses to challenge. The present study examined chaotic living conditions, sleep problems, and responses to academic challenge for 96 economically disadvantaged children enrolled in a Head Start preschool. Caregiver interviews provided information regarding chaotic living conditions of residential crowding, noise, and family instability, as well as child sleep problems. Tasks individually administered to children provided measures of responses to academic challenge. Chaotic living conditions statistically predicted helpless/hopeless responses to academic challenge, and sleep problems partially mediated this relationship. Implications concern pathways of ecological risk and diversity in the school functioning of economically disadvantaged children.