Collected longitudinal data from rural, African American, single mother-headed families with young adolescents to examine longitudinal links between contextual risks, parenting, and youth outcome. Accumulated risks related to lower levels of the competence-promoting parenting practices that were linked directly with youth outcomes via youth self-regulation. Parental involvement, support, and vigilance and youths' development of self-regulation enhanced development among youths growing up in challenging circumstances. (Contains references.) (SM)