Wonsan has been in the spotlight of the global media during the Kim Jong Un era for its military and economic importance. Despite the growing interest in the city, little is known about how Wonsan was rebuilt from almost complete destruction after the Korean War. This study examines how Wonsan’s reconstruction plan changed from 1953 through 1963 and analyzes the reasons for the changes. This paper argues that, influenced heavily by Soviet urban planning, the early city plan of Wonsan was ideal in form and ambitious in scale. However, since full-scale reconstruction began in 1958, Wonsan’s city boundaries have shrunk and become almost the same as the old city limits that were in place during the Japanese colonial period. In addition, as the reconstruction progressed, the plan transformed to emphasize the city’s geographic characteristics and its identity as a coastal tourist city. The resulting asymmetric and dynamic composition remains an important compositional principle in Wonsan’s urban planning to this day. Unlike the splendid reconstruction of Pyongyang, where human and material resources were concentrated, Wonsan’s rebuilding was the result of a trade-off between ambitious ideals and limited resources. Using Wonsan as a case study, this paper seeks to reveal the difficulties and compromises encountered in the reconstruction of North Korean provincial cities that have been long obscured by the exemplary rebuilding of Pyongyang.