The main task of planning documents is to achieve maximal rationality in the use of space, spatial resources, and balanced territorial development. The preparation of plans is regulated by a legislative framework, which embraces multiple phases and stakeholders. In a perfect planning process, it would be expected that all the elements are well coordinated and brought to common understanding, but in reality, obstacles and challenges can occur in any of these steps, especially in the implementation phase. Although a plan is fully prepared to be practiced, its implementation might be omitted. Therefore, this article analyzes the full process of spatial and urban planning from the perspective of plan implementation. The methodology is based on a combination of different data collection methods (interviews, fieldwork, direct observation) with the analysis of plans and the particular mention of those plans that picture the implementation issues the most. Also, legislative acts and semi-annual and annual reports on the achievements of the local government budget are analyzed. The approach indicates that plan implementation depends the most on the willingness of the government to perform changes in the system and to peruse punitive policy comprehensively. Although it is about implementation at the local level, the success primarily depends on clear definitions given in the legislative acts, freedom of the local communities to make their own decisions, and financial decentralization, side by side with the regional and local circumstances, institutional technical and staff capacities, and application of participatory planning that involves actors from various sectors.