This article reviews trends in school-to-work transitions since the 1970s and argues that educational expansion (more young people extending their school and college careers) is a large part of the problem, rather than an actual or potential solution to young people's transition difficulties. The causes of educational expansion are identified as more ambitious parents and young people, educational institutions seeking 'bums on seats', the changing occupational structure, and government policies. The reasons why extended education inevitably fails to fulfil its promises to more and more post compulsory students are outlined; the article then concentrates on labour market outcomes for earlier leavers. Their risks of unemployment remain stubbornly high, despite new and allegedly improved training schemes, more relevant courses and qualifications, New Labour's New Deal, and Connexions. The article explains why adding more rungs to educational ladders will only exacerbate school-leavers' difficulties. (Contains 4 tables.)