This article argues that the training and employment policies of Chile's transition governments since 1990 have failed significantly to promote the development of human resources and occupational citizenship, and identifies key structural and political causes. In particular, the weak development of the property rights of labour and of markets in skill are seen as enduring economic and institutional legacies of the period of dictatorship which continue to constrain key areas of economic development as well as social citizenship rights. The article advocates an analysis of citizenship and skill development that identifies the problem of institutional coordination between a range of different services in labour markets. It suggests that the social organisation of skill markets in Chile systematically discriminates against long-term investments in workers. Hence, even in Chile where economic reformers have sought to maximise markets, decisions on skill investments are, to an important degree, conditioned by power relations and organisational inertia inside individual firms and, at the aggregate level, by the selective channelling of information and the (unplanned) institutional structuring of training supply.