This paper considers the risks to Early School Leaving (ESL) as perceived by young people who are Early Leavers or at-risk of Early Leaving, and their educators in one region in South England. It draws on 38 interviews and focus groups with 39 young people and 53 adults working in various roles across 11 educational settings including mainstream and specialist schooling, alternative learning provision and vocational education and training as well as the local authority. Guided by a holistic framework to examine risks to ESL (Author 1 et al. forthcoming) the paper analyses findings according to five different categories of risk: personal challenges; familial circumstances; social relationships; institutional features of school/work; and structural factors of policy, economic disadvantage and the educational system. Findings highlight that while educators focused upon structural factors and personal challenges, young people themselves saw social relationships and institutional features of school as the most significant influencers on ESL risk. The contribution of this paper is two-fold; firstly in presenting a comprehensive analysis of the multiple risk factors to Early Leaving; and secondly in reflecting on the difference in emphases between young people’s perspectives of the key constituents of risk and those of the educators who support them.