Due to poor political-economic management, the transport sector in North Korea suffers from grave problems that are cyclic, negative-sum, path-dependent in nature. The constellation of problems not only undermine the Stalinist state’s development, but the problems in the structure, processes, and circumstances surrounding North Korea’s transport sector have gone beyond the threshold of no return with very little remedies available. To comprehensively conceptualize the troubled state of North Korea’s transport sector and their operations, one needs to examine the topic from the political-economic, socio-economic, socio-political, and security viewpoints. Focusing on long-distance public transport, this study aims to conceptualize the pervasive, inter-relating nature of the key problems in North Korea’s transport infrastructure and its operations. The study will reveal not only the extent of the problems caused by the North Korean regime, but also raise important questions to deal with the North Korean issue and the future of the Korean peninsula.