Despite predominantly lower social class origins, the second generation of established immigrant groups in the UK are now attaining high levels of education. However, they continue to experience poorer labour market outcomes than the majority population. These worse outcomes are often attributed in part to their disadvantaged origins, which do not, by contrast, appear to constrain their educational success. This paper engages with this paradox. We discuss potential mechanisms for second-generation educational success and how far we might expect these to be replicated in labour market outcomes. We substantiate our discussion with new empirical analysis. Drawing on a unique longitudinal study of England and Wales spanning 40 years and encompassing one per cent of the population, we present evidence on the educational and labour market outcomes of the second generation of four groups of immigrants and the white British majority, controlling for multiple measures of social origins. We demonstrate that second-generation men and women’s educational advantage is only partially reflected in the labour market. We reflect on the implications of our findings for future research.