The United Nations Security Council's sanctions powers under Chapter VII of the Charter are regarded as an essential tool for ensuring international peace and security. However, it is also argued that sanctions regimes can be ineffective, as some do not seem to achieve the goal set by the Security Council. This paper assesses the legal limitations of the Security Council's sanctions system through the analysis of the sanctions regime against North Korea. After considering the theoretical and legal framework for adopting sanctions, an assessment of the implementation of the current sanctions against North Korea reveals several legal limitations to its effectiveness. Firstly, the Security Council is restricted by international law standards when acting under Chapter VII. Secondly, the normative content of the Security Council's resolutions against North Korea lacks specificity. These unclear sanctions and their complexity limit their proper implementation. Finally, the current implementation process is limited by the asymmetry between the Member States' discretion power and the Sanctions Committee's lack of enforcement power. The sanctions regime can therefore not be considered successful. The Security Council adopts ever stricter resolutions, and North Korea continues to find new ways to evade them. As Chapter VII does not seem to be able to resolve this stalemate, considering new alternatives might be necessary.