This article arises from case studies in 2006 of 20 businesses in Samarkand (Uzbekistan), surveys of their up to 30-year-old employees (r = 419), follow-up interviews with eight of these employees, and matched samples in Almaty (Kazakhstan) and Bishkek (Kyrgyzstan). The main difference between education in Samarkand (and Uzbekistan in general) and the comparator locations was that the former was maintaining government-regulated academic and vocational tracks through upper secondary and higher education which were intended to prepare young people for employment at different levels in different industries. In contrast, in Almaty and Bishkek, since 1991 there had been unregulated expansion of general upper secondary and higher education. The evidence suggests that Samarkand was deriving no clear benefits from its particular educational provisions in terms of the smoothness of young people's education-to-work transitions, the satisfaction of young workers with their jobs or employers' satisfaction with their recruits, and only a minority of the Samarkand businesses appeared to be saving on initial training costs. Furthermore, none of the cities' educational provisions appeared to be stimulating the development of training cultures within firms, and Samarkand's institutions appeared distinctly less successful in motivating young people to invest in and plan their own career development. However, preventing the unregulated expansion of academic secondary and higher education in Samarkand was resulting in cost savings for young people and their families. Meanwhile, maintaining fully state-funded vocational routes in upper secondary education was increasing the costs of education to the government. It is argued that, although in itself not a sufficient explanation, a necessary condition for the maintenance of employment-related tracks in education is likely to be not just state regulation, but also a willingness and ability on the part of governments to bear a higher proportion of the costs of education and training than in unregulated systems where more of the costs can be borne by young people and their families. (Contains 7 tables.)