The relevance of the study is related to the increasing cases of various destructions in the interaction between students (bullying, cyberbullying, addictive behavior, armed attacks), which are considered as variants of students’ maladjustment as a result of deep sociocultural transformations in society. The purpose of the study is to present the author’s classification of the types of subjective riskiness of students based on the analysis of their psychological resistance to the socio-cultural risks of the educational environment of the school and to describe them in the context of personal characteristics. The study sample consisted of 3232 students of secondary schools of the Republic of Tatarstan aged 12 to 16 years. Students who voluntarily agreed to take part in the study filled out in writing a bound questionnaire, which included the author’s methodology “Index of socio-cultural safety of a schoolchild” and “R. Cattell’s 14-factor personality questionnaire”. The study was conducted anonymously, the respondents were required to indicate their age and gender. Statistical research methods are cluster analysis, comparative analysis (Student’s t-test), descriptive statistics. The subjective riskogenicity of students is considered from the standpoint of the problems of psychological resistance to the sociocultural risks of the educational environment, which determine the complexity of interaction in the “subject-contextual” system of the educational environment. The author’s typology of subjective riskiness of students is presented: vulnerable type, disintegrated type, maladaptive type, autistic type, adaptive type. The specifics of students’ personal characteristics are described depending on the type of their subjective riskiness. Conclusions: the hypothesis was confirmed that students with problems of psychological stability, constituting a certain type of riskiness (autistic type, disintegrated type, maladaptive type, vulnerable type), in contrast to the adaptive type, have characteristic personality traits that cause the complexity of interaction in the “subjectively -contextual” system of the educational environment. The maladaptive type is distinguished by impatience and the desire to dominate. The disintegrated type characterizes social courage and reduced sensitivity to threats. The vulnerable type is characterized by depression, anxiety, sensitivity to acceptance in the reference group, increased frustration, and the autistic type of students is characterized by reduced responsibility, determination and self-control. Practical application of the results. Identification of the type of subjective riskiness of students opens up the possibility for the individualization of the educational process and the implementation of timely preventive measures to prevent the socio-psychological maladjustment of children and adolescents.