This study is based on a statewide longitudinal sample of adopted foster youth and explores the relationship between early pre-adoption risk factors and subsequent elevated levels of psychopathology symptomatology. One central goal of the study was to evaluate the impact of preadoption stressors (prenatal drug/nicotine exposure, early maltreatment, chaotic foster care history) on the 293 adopted foster children's short- and long-term psychosocial functioning at ages 2, 4, and 8 years post-adoption. An additional objective pertained to measuring how post-adoption attributes (adoptive parents' appraisals of their readiness for this type of adoptive placement and of their parenting style using the HOME scale) contributed a partial mediating influence to the children's functioning. The effects of risk and protective factors were examined through linear regression analyses. The strongest risk factors for the display of behavior problems were sexual abuse, neglect, and having been placed in multiple foster homes. Crucially, lack of parental readiness contributed a substantial increment to the overall models. In addition, longitudinally, the behavior problems remained stable across time. The implications of these findings for the development of services and interventions targeted for adoptive families are discussed.