Experiencing the death of a parent during childhood is associated with a variety of difficulties, including lower academic achievement, that have implications for functioning in childhood and adulthood. This study examines effects of the Family Bereavement Program (FBP), a preventive intervention for parentally-bereaved youth and their caregivers, on grade point averages (GPA), educational expectations and job aspirations of youths 6 years after the intervention. A total of 244 bereaved youths ages 8–16 and their caregivers were randomized to either the FBP or a comparison group that received books about bereavement. Assessments occurred at pretest, post-test, and 11-month and 6-year follow-ups. Direct program effects on educational outcomes and job aspirations 6 years later were non-significant, although the program improved educational expectations for children with fewer behavior problems at program entry, and GPA for younger children. Mediational pathways for program effects on educational outcomes were also tested. Program-induced improvements in effective parenting at 11-month follow-up were associated with higher GPAs at 6-year follow-up for youth who were younger or for whom more time had passed since the loss. Program-induced improvements in parenting and teacher-rated youth mental health problems at the 6-year follow-up mediated program effects on youths’ educational expectations for those with fewer behavior problems at program entry. The implications of these findings for understanding processes related to academic and educational outcomes following the death of a parent and for prevention efforts to help bereaved and other high-risk children succeed in school are discussed.