The issue of conditional early discharge has recently become one of the highly debated topics among legal scholars. Research papers and court practice both indicate that there are a number of problems in the enforcement of this institute by courts. Thus, the authors doubt the position of the Supreme Court of the Russian Federation when granting a person, whose conditional discharge on one of the sentences was previously cancelled, a new opportunity for conditional early discharge after that person has served the prison sentence according to point «в», part 3, Art. 79 of the Criminal Code of the Russian Federation. The authors argue that legislators should eliminate an opportunity to grant conditional early discharge to persons guilty of gravest crimes as well as those guilty of repeat crimes of small and medium gravity. The paper stresses the controversy in the disposition of part 5, Art. 79 of the Criminal Code of the Russian Federation that gives a person sentenced to life imprisonment an opportunity to apply to the court for conditional early discharge. The authors present some measures aimed at the elimination of these contradictions; in particular, they suggest adding a special part to Art. 79 of the Criminal Code of the Russian Federation that would directly prohibit a court from granting conditional early discharge to repeat offenders as well as those guilty of extra grave crimes. Besides, Art. 79 of the Criminal Code of the Russian Federation should clearly state that conditional early discharge cannot be granted to those who have not admitted their guilt and have not repented their actions.