Abstract: Introduction. The research is aimed at studying the difficulties of convicts’ resocialisation as well as individuals subjected to administrative supervision. The relevance of the study is based on the social significance of countering recidivism, reducing the level of offences, as well as the necessity to gain new scientific knowledge concerning the resocialisation factors. The problem of the study is in the lack of a comprehensive understanding of resocialisation factors, diverse ideas about personal and interpersonal characteristics, and social factors disrupting resocialisation process. Research methods include theoretical methods of cognition: generalisation, categorisation and systematisation of information regarding the factors contributing to the resocialisation of convicted individuals; empirical methods of cognition: questionnaire, mathematical and statistical analysis - descriptive statistics, exploratory factor analysis, comparative analysis – Mann–Whitney U-criterion. Results of the study. The diverse socio-psychological causes of resocialisation disorders were generalised in the form of a three-component model describing personal characteristics, interpersonal relations and social conditions. The empirical study of perceptions of the causes of resocialisation was carried out. The sample included individuals serving sentences in correctional institutions of the Federal Penitentiary Service of Russia, individuals under administrative supervision (n = 252) and law enforcement officers (n = 232). Conclusions. The theoretical model of resocialisation difficulties has been verified. Differences in the perception of the reasons causing resocialisation failures in the group of convicted individuals and law enforcement officers have been established. Recidivists are characterised by the desire to blame the social environment, underestimation of their own negative personal characteristics and social conditions. These include alcohol and other addictions, their manipulation of others, retention of a criminal lifestyle, idleness and hedonism. Law enforcement officers are characterised by increased attention to the conditions of social functioning and negative personal characteristics of ex-convicts. The results broaden and clarify scientific ideas about the factors that impede resocialisation, and the tools developed in the course of the study have been tested and are applicable for the practical study of a set of socio-psychological problems of integration of convicted individuals into the community.