1. Introduction The rise of youth unemployment regarded as the failure of transition from school to work gave good grounds for examining this transition. Estonia is not an exception. In the early 1990s young people were considered as the most privileged age group, whereas in the late 1990s it became evident that a lot of problems were connected with the entry into adult life, more specifically, into the labour market. Although unemployment in general, as well as the youth unemployment, are relatively novel phenomena in Estonia, the gap between the unemployment rates among the younger and the older age groups is continually widening (Helemae and Voormann 2003). Our intention is not to concentrate on the analysis of the young as a specific age group. Instead, we prefer to compare labour entrants with experienced workers (1) because previous studies have demonstrated that the national organisation of the educational system as well as the labour regulation influence the biographical timing of the transition (Couppie and Mansuy 2003). The category of new labour entrants is useful because it combines the characteristics of the youth's position ...towards the education and training system with the experience accumulated on the labour market (Couppie and Mansuy 2001a:24). Compared to the rest of the labour force, new entrants are defined by their lack of labour experience. According to the insider-outsider theory, they are considered as outsiders. There is a great number of empirical studies on school-to-work transitions carried out in the European Union countries (see for example Hannan et al. 1997, Shavit and Muller 1998, Kerckhoff 2000, Smyth et al. 2001, Kogan and Muller 2003, Muller and Gangl 2003) while the studies conducted in the Central and Eastern European countries are quite rare (see for example Cedefop 2001, Robert and Bukodi 2002, Toomse 2003, Kogan and Unt 2004). The present paper will analyse the differences in the unemployment rates between labour entrants and experienced workers, the incidence of unemployment among labour entrants from the perspective of individual educational achievement, and explore how the educational stratification of unemployment varies across different countries. Previous studies have shown that European countries differ markedly with respect to some core aspects of youth transition experiences (see Gangl et al. 2003). The countries to be compared are Estonia and the EU countries. The core of our interest concentrates on the aggregate effectiveness of youth labour integration in Estonian institutional context. The study will be guided by the following main questions: Are there any differences in unemployment risks between labour entrants and experienced workers? If so, in what way does the institutional set-up in different countries shape these differences? Which role does education play with regard to labour entrants' risk of unemployment? To what extent does the importance of education depend on the career stage on which individuals are at the risk of unemployment? Is there evidence to be found about distinct national linkages between education and unemployment risks? As European educational systems and labour institutions differ considerably in their structures, these structures have considerable theoretical potential for explaining cross-national differences in transition patterns (Shavit and Muller 1998, Muller and Gangl 2003). The starting point for the formulation of the hypotheses is the assumption that labour institutions and educational systems have an impact on the labour entry process. Comparing the educational systems as well as labour institutions in Estonia and in the EU countries, we could formulate the hypotheses about labour entry process in Estonia using the classification results from previous studies. The paper draws upon data from the Estonian Labour Force Survey 2002 and also data from the ELFS 1997 about European Union countries published in Cedefop report (2001). …