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Care leavers have been known to have poorer educational trajectories as compared to the general population (Gypen, et al., 2022; Wade & Dixon, 2006) and are more predisposed to the ‘not in education, employment or training’ (NEET) phenomena (HM Government, 2013; National Audit’s Office, 2015; Van Breda & Dickens, 2017). Care leavers are identified as individuals who lived within residential care such as a Children’s Home (The Care Leavers’ Association, 2014; University of the Highlands and Islands, n.d.) and youth who reside in this institutionalized setting are undoubtedly one of the most vulnerable groups within society (United Nations Children’s Fund, 2002). International literature has well established that while living in residential care, behavioural challenges persist and there appears to be a lack of psychological attention to these young persons (Erol, et. al, 2009; Goffe, et. al, 2009). Due to the negative institutional settings for those in residential care and their poor trajectories as care leavers, the question arises as to whether these psychosocial inequalities have contributed to the negative educational attainment outcomes seen amongst this vulnerable population. In response, a Barbadian study which explores the lived experiences of care leavers’ transition to independent living, has brought to the fore the importance of educational attainment in care leavers’ success to independent living. The research which is crouched in Urie Bronfenbrenner's Ecological Systems Theory and Erik Erikson’s Psychosocial Stages of Development, demonstrates both the social systems and psychological decisions these care leavers must navigate. Drawing from Barbadian experiences, this paper discusses the importance of educational attainment in facilitating positive care leaver outcomes and the critical mentorship role of educators in the lives of care leavers.