On September 26, 2023, the Constitutional Court declared unconstitutional the provisions regulating the distribution of anti-North Korea leaflets under the Act on the Development of Inter-Korean Relations. As a result, the issue of the sharp conflict at home and abroad surrounding the distribution of anti-North Korea leaflets and its regulations, which has gradually worsened since the 2000s, appears to be coming to an end. The government also appears to be taking various follow-up measures in line with the above Court's decision to find it unconstitutional. Meanwhile, the opinions of the above Court judges were divided on whether the regulation on the distribution of anti-North Korea leaflets was a restriction on the content of expression or a restriction on the method of expression. Depending on how you interpret it, the degree of restrictions on freedom of expression may vary. In particular, the seven people's unconstitutionality opinion viewed the regulation of the distribution of anti-North Korea leaflets as a restriction on the content of expression and argued that strict standards should be applied to such restrictions. At the same time, even if the distribution of leaflets against North Korea is not regulated by criminal punishment, freedom of expression is protected through the application of Article 5, Paragraph 1 of the Act on the Performance of Duties by Police Officers or the introduction of a system similar to the reporting system under the Assembly and Demonstration Act. It was believed that there were less restrictive means available. In other words, it took the position that the provisions regulating the distribution of leaflets against North Korea violate the principle of minimal infringement. However, apart from the fact that the anti-North Korea leaflet regulations were declared unconstitutional, if leaflets continue to be distributed to North Korea in the future, tensions between North and South Korea will increase and safety issues for residents in the border area may continue to be raised. In addition, if a political or security environment is created in the future that actively supports regulation of the distribution of anti-North Korea leaflets, the removal of the matters presented by the above Court as reasons for its decision to be unconstitutional and then the possibility of attempting a new form of legislative regulation won’t be completely excluded. Therefore, a review of means that can less restrict freedom of expression suggested by the above Court's unconstitutionality opinion is required from a normative and realistic perspective. In this article, we examined the gist of the above Court’s decision and analyzed and evaluated the decision of the above Court, focusing on the normative and realistic limits of regulating acts such as the distribution of leaflets to North Korea - especially the application of Article 5, Paragraph 1 of the Act on the Performance of Duties by Police Officers or the introduction of a system similar to the reporting system under the Assembly and Demonstration Act - and then drew implications.