This paper applies a conceptual framework of five key categories (personal challenges, social relationships, family circumstances, institutional features of school/work, and structural factors) to consider the comparative contexts of risks to Early Leaving (EL) in key regions within Spain with a high national level of EL and England, a nation with low relative EL. The two-country comparison draws from 77 interviews and focus groups with 309 educational stakeholders across 21 settings involved in the European Commission funded project [Orienta4YEL]. Key findings are elicited in highlighting the points of convergence and dissonance within data patterns. Notwithstanding the high level of interaction between them, the most significant risk categories identified were ‘personal challenges’ linked to ‘family circumstances’ for Spain and ‘structural factors’ for England. Key differences can be partly attributed to the different vulnerability groups of at-risk (of EL) young people, as well as differences in the geographical and socio-cultural regions. There is, however, convergence in findings with respect to the key structural factors seen to be barriers to EL, specifically with respect to the impact of socio-economic disadvantage and challenges raised with regard to the educational system and educational policies, as well as the role of young people’s relationships.