Given the increasing complexity of urbanization and the expansion of public institutions' interventions in the urban development process, the need to rethink regulatory practices and pay attention to the principle of legitimate expectations as one of the fundamental components of citizens' legal security has been explained. The importance of the research is that the instability of urban regulations and frequent changes in development plans have weakened public trust, reduced legal predictability, and led to widespread conflicts in the urban management system. The research method in this study is descriptive-analytical, and the main research question is how the desired pattern of urban regulation with an emphasis on the principle of legitimate expectations can lead to improved legal security and the efficiency of the urban development system. The research findings show that the lack of stability of regulations, unpredictable changes in urban plans, weak guarantees of implementation, and the absence of compensatory mechanisms are among the most important factors weakening legitimate expectations in the urban management system. The results also indicate that institutionalizing the principle of legitimate expectation through the consolidation of urban planning rules, transparency in decision-making, observance of acquired rights, strengthening judicial supervision, and citizen participation can lead to increased public trust and reduced urban conflicts. The results of the study confirm that the desired model of urban regulation is one in which the principle of legitimate expectation is considered as a guiding criterion in all stages