The article summarizes the empirical data obtained by P. N. Kolotinsky in 1913–1926 by means of questionnaires of graduates at the Yekaterinodar Gymnasium and the Krasnodar Soviet Labor School, as well as the questionnaires of graduates of Krasnodar schools in 1997, 2006, 2014 and 2020 respectively.The research focused on the values and ideals of high school students, with an important set of questions relating to school attitudes, favorite subjects and career choices. Although a significant number of questions have remained the same, the questionnaire procedure itself changed over the years, and the number and gender composition of the respondents varied considerably, the socio-political context of the surveys has a common feature: all studies have been carried out at the time of radical turns of history, in periods of social transformation. The authors pursued the following scientific objectives: to define the dynamics of attitudes towards school and its social role, to identify changes in the perception of occupations and preferences in school subjects, and to evaluate the perception of the experience of distance learning during the coronavirus pandemic. The methodology of the study included a questionnaire design, whose results were verified in four expert sessions in 2020. The school continues to be one of the basic social institutions that ensure the continuity of society and the socialization of generations. The social role of school as an important mechanism for the authorities to influence the formation of the values and attitudes of the population enhances in times of social and political transformations. The positive perception of the school throughout the period under review has lost its emotional intenseness, and a neutral and pragmatic perception of the school as a necessary stage for further education prevails. The vocational guidance of high-school students is influenced by a combination of factors (changes in the industrial structure of the economy, the socio-political environment, prevailing social stereotypes, the material well-being of the family, etc.) and the demands of society, formulated, inter alia, in numerical targets for admission to budgetary seats. The experience of distance learning is perceived by high school students as ambiguous and contradictory, and distance education has exacerbated the digital divide in property and generational dimensions.