Introduction. The article deals with the problem of psychological adaptation of adolescents to difficult life situations. The existing theoretical approaches to understanding the phenomenon of psychological adaptation are analyzed, the concepts of “difficult life situation”, “critical situation” are considered. Particular attention is paid to the analysis of the psychological specifics of the coping behavior of adolescents. The group of subjects who are in a difficult life situation was formed from pupils of the State Committee for Education and Science of the Republic of Moldova “Republican social shelter for children and adolescents ‘Nadezhda’ ”. Materials and Methods. In the course of the empirical study the following methods have been used: the projective method “Psychological autobiography” by the authors L. F. Burlachuk and E. Yu. Korzhova, the projective method “Man in the rain” by the authors A. Abrams and A. Emchin. To process the obtained empirical data, methods of mathematical statistics were used: the Mann – Whitney U-criterion and the φ* criterion – Fisher’s angular transformation. Results. According to the results of the empirical study, most adolescents of the 2nd group were characterized by the manifestation of passivity, lack of energy, stiffness, rigidity in difficult life situations, which generally confirms the weak representation of problem-oriented coping strategies in the coping behavior of adolescents. Discussion and Conclusion. The pupils of the orphanage turned out to be characterized by depressive states, possibly determined by the unfavorable social situation in which they found themselves, and in which they are most likely to experience deprivation of support from significant people. On the basis of the study carried out, psychological recommendations have been formulated to improve the effectiveness of adolescents’ psychological coping with difficult life situations, which can be used in the professional activities of psychologists – in professional counseling and psychocorrection, in the work of a teacher-psychologist, school psychologist and other specialists. These recommendations take into account, first of all, the importance of developing problem-oriented coping strategies in adolescents based on an objective and critical analysis of the cause-and-effect relationships of difficult situations.