This paper deals with the employment insecurity in the context of labor market dysfunction and changing institutional structure of the economy. We consider the actorsʼ behavior in the labor market as affected by the institutional factors. Employment insecurity and associated precarity processes are essenstial for young people entering the labor market. Qualitative methodology allowed us to identify the behavioral preferences of the informants through the in-depth interviews. We have conducted and analyzed 17 in-depth interviews with the university graduates. The research findings showed that the graduates are generally aware of the problems associated with unstable employment in the Russian labor market. They are relatively loyal to informal employment during university studies and for the initial few years after graduation. We focus on the graduates’ perception of the precarization processes in the context of the labor marketʼs structural opportunities. The gap between educational and economic policies and the emergence of institutions that create sustainable rules for the professional and personal development of the employees is an important cause of youth unemployment. The behavioral strategies of university graduates are associated with three main groups of factors: the existing institutional constraints on the labor market, adaptation to the demand structure in the region (city) in its competence area, and the level of competence of the graduate and his/her self-assessment of these competencies and their relevance to employersʼ modern requirements. The challenges of precarious employment are addressed by graduates in the context of competition and the need to improve their skills.