Results indicated that African-American boys had lower expectations for their educational attainment than did African-American girls. Parents and teachers also held lower educational expectations for African-American boys than for African-American girls. These findings remained significant after controlling for school achievement. Parental educational expectations were found to fully mediate the relationship between youths’ gender and their educational expectations for themselves. However, several school-based factors, such as positive teacher expectations and positive school environment, served as protective factors from the influence of parents’ low educational expectations. The findings add more evidence to a burgeoning research agenda showing the positive impact school-level factors can play in the lives of youth who have compromised family processes. Data were drawn from the Child and Family Study (CFS) of the New Hope Project, an anti-poverty initiative implemented in two low-income neighborhoods in Milwaukee, WI. Future research should focus specifically on the influence of co-parents, extended family members, and mentors in the educational expectations of African-American youths. The current study focused on 301 African-American primary caregivers and 466 of their children, ages 6 to 16 years. Families completed a series of interviews and teachers of participating children completed mailed questionnaires. Variables under analysis included youths’ educational expectations, parents’ educational expectations for their children, teachers’ educational expectations for their students, perceptions of the school environment, youths’ academic achievement, and socioeconomic status. Ordinary Least Squares regression models were used to analyze the data. Tables, figures, footnotes, references