This paper discusses the cleavage of North Korean system for determining the unstable structure of economic security and the complexity. Using the perspective of complexity theory and the notions of self-organization and evolution as analytic tools, the research focused on North Korean markets. The research 1) examined the path of the North Korean market’s self-organization, 2) clarified the path of the market’s evolution while putting emphasis on dynamic variations from the self-organization and the unfolding, 3) deduced market agents and the features 4) and considered their interactions and the features. In the results of research, the cleavage of the system shed a lot of light on the structural instability of economic security as well as the complexity. North Korea’s political economic system, where the planning and the market coexist, includes both “the controls and coordination on markets from above” and “the spread of markets by needs from below” which is a base for the improvement of markets. And it shows various aspects of coordination, cooperation, and conflict in a big frame of attacks and defense. Therefore, the path of North Korean market development does not merely express the vitality from below, but includes the process of coordination and decline by attacks on the market from above.