After being derogated several times, the institute of multiple recidivism was re-incorporated into the Republic of Serbia’s positive criminal legislation with the intention of giving intentional perpetrators of crimes punishable by imprisonment, who were previously convicted at least twice for criminal offenses committed with intent to imprisonment for at least one year, harsher penalties and disabling them from committing criminal offenses in the future. Numerous disputed scenarios required national jurisprudence to find solutions, with the challenges of calculating the criminal range and the level of the lower threshold of the imposed criminal sentence standing out in particular. The observed institute was analyzed primarily through the prism of rationality, justification, and expediency of the current normative solution, within which the author attempted to provide answers to potentially contentious issues. The findings of the conducted research indicated that the new concept of the institute of multiple recidivism is incorrect because the threshold of half the penal range is excessively high and does not leave enough space for the court to objectively weigh the circumstances of each specific case. Furthermore, the findings suggest that in some cases, an approach based on alternative measures may be a more convenient solution, as well as that the application of the existing legal solution regarding the observed institute is merely legitimate in relation to some categories of perpetrators who are declared “incorrigible.” The conducted research concludes that, due to the arguments presented in the paper, there is a high likelihood that the institute of multiple recidivism will again be derogated from the Republic of Serbia’s legislation if the provision of Art. 55a of the Criminal Code remains unchanged.