It is now nearly thirty years since Margaret Thatcher and her Conservative administration introduced the Assisted Places Scheme (their first education policy) and over ten years since New Labour abolished it. The Scheme, which was designed to provide a ladder of opportunity for academically able students from poor backgrounds to attend private schools, is of more than historical interest. It can be used to illuminate enduring sociological concerns about the relationship between home and school. This paper draws on retrospective interview data to reveal how the Scheme was experienced by its more disadvantaged beneficiaries. Revisiting classic sociological analyses from the 1960s and 1970s, it unravels the complex interactions between home background, friendship networks and school cultures and shows how these contributed to contrasting experiences of commitment, detachment, estrangement and alienation. These differing modes of engagement with schooling appear to have had lasting effects on our respondents and influenced their subsequent careers and orientations.