This article aims to analyse the psychological and legal aspects of preparing individuals serving custodial sentences for release. From a psychological perspective, an analysis was conducted of the relationships between stress generated by the perception of difficult situations (past, present, and future) and positive motivation toward drug use. The study involved 267 individuals serving custodial sentences. The Own Life Assessment Questionnaire by I. Niewiadomska and the original Questionnaire of Prisoners’ Attitudes Toward Drug Use, developed by participants of a master’s seminar at the KUL Study Centre at the Lublin Remand Centre, were used. Statistical analyses included Pearson’s r correlations and linear regression. The results revealed statistically significant positive relationships between the intensity of stress generated by experiencing past, current, and anticipated difficult situations and positive motivation to use drugs. Regression analysis confirmed that anticipated future difficult situations constitute a significant predictor of positive motivation toward drug use. From a legal perspective, the statutory framework for the period of preparation for the release of individuals serving custodial sentences was presented. It was also demonstrated that the relationships identified in this study between experiencing difficult situations and positive motivation toward drug use should be considered an important aspect in assessing the risk of recidivism among individuals leaving correctional facilities. Attention was also drawn to the need to introduce standards in the field of psychological penitentiary assessment, particularly in diagnosis for penitentiary resocialization, penitentiary therapy, and/or activities aimed at preparing prisoners for functioning in conditions of freedom.