This article highlighted the specific nature of the execution of custodial sentences in the Republic of Moldova. Similarly, some theoretical and practical aspects of the current difficulties encountered in achieving the purpose of the deprivation of liberty were approached through the proper application of progressive and regressive regimes. Special importance has been given to the identification of the current regulations that determine the placement in different types of prisons with the three detention regimes. Also, this scientific paper draws attention to the necessity to carry out studies aimed at contributing to the formulation of proposals for amending the normative and institutional framework in order to enforce custodial sentences, including the current infrastructure conditions. For a suitable weighting of the necessary efforts in the process of applying new detention regimes. Thus, the legal analysis of the present provisions has attempted to make the present work useful both to the justices and to the academic environment regarding the current realities concerning the application of detention regimes and the need for intervention in this field.