The social and economic changes, which happened for the last two decades in Russia, created essentially new context to which both the education system and participants of labor market – employers and employees have to adapt. How successful was this mutual adaptation? To what degree “outcome” of education system (qualification and educational potential) are accepted by the Russian labor market? In the article on the basis of 120 expert interviews, conducted with employers, recruiting agencies, regional officials, top university representatives – we are searching the answers, exploring the trends in this domain. It is shown that main tendency – discrepancy of the available quantity and quality of the trained university postgraduates does not meet structure and demand shown by employers. In some cases, universities and students provide simulation (simulacrization) of vocation training. The reason for this can be found in structural unemployment and in considerable lag of the level of educational sphere from real requirements of labor market. Underexploitation of qualification, competencies and educational potential confirms existence of effect of ‘rupture’ of the educational services spere from requirements of labor market.