This article addresses the question of whether the first job functions as a ‘stepping stone’ or as a ‘trap’. It does so by using individual longitudinal data to estimate the consequences on future occupational attainment of entry into the labour market via (a) ‘under-qualified’ jobs or (b) via temporary contracts. A cross-national comparison of West Germany, Great Britain and Italy allows assessment of the impact of different labour market structures on this allocation process. With regard to ‘under-qualified’ positions, the findings are not consistent with the stepping-stone hypothesis but provide some support for the entrapment hypothesis. Despite the greater mobility chances of over-qualified workers, the initial disadvantage associated with status-inadequate jobs is not fully overcome during their future careers. The article shows, however, that the negative effects are not due to the mismatch as such but rather to the relatively lower level positions. These effects are mediated by the national labour market structure, with the British flexible model providing the best chances of making up for initial disadvantages, and the more tightly regulated and segmented markets in Germany and Italy leading to stronger entrapment in lower status positions. No negative effects of the type of contract are found for later occupational positions in any of the countries.