The relevance of the study is determined by the growing number of teenagers with signs of deviant behavior and, as a result, by the necessity to organize a system of effective work with them. The declared multi-paradigm approach allows us to select the forms and methods of work that optimally correspond to the context of interaction. The study objective is to identify the most common approaches to working with so-called diffi cult adolescents in liberal, socially oriented, and learner-centered paradigms of a person’s upbringing. The study points out vertical paradigms, which determine the specifi cs of educational practices in diff erent historical periods, and horizontal paradigms, which determine their variability at present. Results: the study presents a brief historical overview of the ways of upbringing and re-educating diffi cult teenagers in the Russian Empire and Soviet Russia; it shows the changes in the preferred ways of upbringing from repressive and punitive to correctional, rehabilitating and re-socializing. The study gives some examples of experimental educational institutions, the practice of which was ahead of the traditional approaches to the rehabilitation and reforming diffi cult adolescents in the liberal paradigm (Rukavishnikov orphanage), in the socially oriented paradigm (Gorky colony, Dostoevsky Commune School, etc.). The unproductive character of a unifi ed approach to determining eff ective forms and methods of working with diffi cult adolescents in a learner-centered paradigm is noted. The study identifi es the necessity of creating a school system of preventive work with those teenagers who are at risk and those who are in tough circumstances. It is suggested that such a system is eff ective if it combines rehabilitation forms and ways of maintaining physical, emotional and psychological well-being which are attractive to adolescents. Conclusions: the format of the learner-centered educational paradigm is optimally matched by an extensive system of psychological and pedagogical support for adolescents. This support should provide teenagers with the opportunity to integrate into diff erent types of pro-social activity at the school, neighborhood, district and city levels. Practical significance: the results of the study can be applied in the educational process to conduct conversations about changes in choosing the approaches to organizing pedagogical interaction. They can also be used by researchers who are involved in the development of applied aspects connected with the interaction with diffi cult teenagers