What has been the trajectory of military cooperation between North Korea and Russia since the end of the Cold War? What are the driving factors and obstacles behind their evolving security relationship? This study aims to assess the level of strategic cooperation in North Korea-Russia relations from 1991 to 2023, providing a structured analysis of the nature and direction of their partnership. The findings reveal that military cooperation between Pyongyang and Moscow has consistently remained at an early stage, reflecting a state of weak alignment. Additionally, the study suggests that significant strategic obstacles are likely to continue limiting the extent of military collaboration in the foreseeable future.