This paper examines the relationship between childhood exposure to cumulative risk and three indicators of psychosocial adjustment in adulthood (educational attainment, mental health, and criminal behavior) and tests three different models (linear, quadratic, and interaction). Data were collected over several time points from individuals who were part of a prospective cohort design study that matched children with documented cases of abuse and/or neglect with children without such histories and followed them into adulthood. Hierarchical multiple regressions compared linear and quadratic models and then examined potential moderating effects of child abuse/neglect and gender. Exposure to a greater number of childhood risk factors was significantly related to fewer years of education, more anxiety and depression symptomatology, and more criminal arrests in adulthood. The relationship between cumulative risk and years of education demonstrated a curvilinear pattern, whereas the relationship between cumulative risk and both mental health and criminal arrests was linear. Child abuse/neglect did not moderate these relationships, although there were direct effects for both child abuse/neglect and gender on criminal arrests, with more arrests for abused/neglected individuals than controls and more for males than females. Gender interacted with cumulative risk to impact educational attainment and criminal behavior, suggesting that interventions may be more effective if tailored differently for males and females. Interventions may need to be multifaceted and designed to address these different domains of functioning.