Abstract: The article presents theoretical and methodological approaches to the study of the social adjustment process of adolescents and introduces the classification of factors influencing this process. There are distinguished macro-factors, meso-factors and micro-factors, nature of their impact on the social adjustment of adolescents and their peculiarities in the Soviet Union and modern Russia. Also, there are considered the changes in socio-political and socio-economic conditions in Russia after the collapse of the Societ Union, associated with the transition from the closed to the open society, from the planned to the market economy. There was revealed the increasing complexity of conditions of adolescents' social adjustment, which accompanied the above-mentioned process: deterioration of families' financial situation, increase in crime, destruction of the political system and government control, social instability, the absence of the state ideology, destruction of the socialistic values, mass media diversity, the spread of the Internet. On the basis of empirical data from two sociological investigations conducted with the difference in 26 years (at the end of the Soviet Union and in modern Russia), there are analyzed peculiarities and results of the adolescents' social adjustment process within the specified periods. There are shown the changes of adolescents' worldview on the issue of survival, health, relationships between people and state and national culture in the last 26 years. There is revealed the nature of the changes in the value structure of adolescents which characterizes the results of social adjustment in different socio-political and socio-economic conditions: the significance of interesting of work, family, relationships between people of different nationalities, ways of spending free time. There is shown how much the structure of these values have changed over the last 26 years and how it can be described in modern Russia. Special attention in the article is paid to the changes of moral values of adolescents: in relationships between people, in relation to their deviant behavior, to moral standards and ideals, to the people representing these ideals. The change in the role of family members in the formation of adolescents' moral values is also revealed in this article. There was made a conclusion that adolescents acutely feel all changes occurring in the society and that these changes have the multidirectional impact on the process of adolescents' social adjustment (they lead to both positive and negative results of that process). The results of studies help to see how the younger generation lives, what they think of themselves and of adults, of society and state, and how qualitative changes in society influence the changes in the process and results of adolescents' social adjustment and in their minds. This knowledge allows us to understand the direction in which the Russian society moves, the future of which is in the hands of modern adolescents.