The current study used a resilience framework to describe youth experiences with their caseworkers, examine the association of youth–caseworker relationship quality with school engagement, and to examine the differential impact of youth–caseworker relationships on youth school engagement by level of youth risk (i.e. posttraumatic symptoms). Secondary data collected from youth in foster care were analyzed via descriptive statistics, correlations, and linear regression with moderation. On average, youth reported relatively high relationship quality with caseworkers. There was substantial variation and developmental differences in youth–caseworker relationship quality. Additionally, current findings suggest that positive youth–caseworker relationships can bolster school engagement. Finally, the study provided support for differential impact theory whereby the influence of youth–caseworker relationships on youth school engagement was stronger for youth with fewer posttraumatic symptoms. Implications for research, intervention efforts, policy, and practice in child welfare, education, and mental health are discussed.