Understanding how we can support children through their learning life course has become a policy imperative, particularly those children from poor homes who would normally be facing a low achiever trajectory. The paper reports on 50 in-depth Child and Family Case Studies (CFCS) that were conducted as part of the Effective Provision of Pre-School, Primary and Secondary Education (EPPSE 3-16) research project. The CFCS was designed as a mixedmethods study in order to look at why and when certain children manage to succeed 'against the odds' while others do not. Using in-depth interviews with students, parents and teachers, quantitative data available from EPPSE and a literature review on risk and resilience, the CFCS provides 'thick descriptions' and explanations of how child, family and school factors interact and contribute to children succeeding against the odds of disadvantage. The study uses over 13 years of data collected from the 50 families and shows that in families with children 'succeeding against the odds', parenting is characterised by 'active cultivation' and that schools, teachers, peers and the wider community contribute to children's academic success by providing emotional, practical and relational support. As a result these children are facilitated and encouraged to develop a combination of positive cognitive and socio-behavioural characteristics that helps them become active agents in their learning life-course. The CFCS provide information that can be of use to both policymakers and practitioners. It has implications for parenting and home-school relations and may serve to inform policies and practices that aim to increase the chances of children 'at risk' and help in closing the gap between those who are academically and socially advantaged and disadvantaged.