Although some risk taking in adolescence is normative, evidence suggests that adolescents raised in conditions of socioeconomic disadvantage are disproportionately burdened with risk taking and its negative consequences. Using longitudinal data from the NICHD Study of Early Child Care and Youth Development, we investigated quality of the early caregiving environment as a potential prospective buffer against the long-term association between childhood poverty and adolescent risk taking. Multicategorical moderation model results indicated that if raised in poverty across age 1–54 months (average family income to needs ratio ≤ 1.02), relative to affluence (income to needs ratio ≥ 6.16), adolescents with histories of secure attachment to caregivers exhibited two times the number of risk behaviors at age 15, whereas adolescents with insecure–disorganized histories exhibited nearly five times the number of risk behaviors. Both early family economic hardship and history of insecure–disorganized attachment remained significant predictors of increased adolescent risk taking, alongside the interactive effect. Probing the interaction's region of significance revealed that history of secure (vs. insecure–disorganized) attachment is associated with protective reductions in risk taking below a family income to needs ratio of 2.24, or about 220% poverty level. Findings support a diathesis–stress model in which children with secure attachment histories are less deleteriously impacted by early socioeconomic adversity than their insecure–disorganized peers.