Limitations of urban constructions in the form of rules and regulations with the aim of controlling city physicaldevelopment is the product of city development plans and documents. Actually, construction rules and regulationsin a metropolis like Tehran is the tool of performing urban development plans and development process in shorttermurban projects and long-term development plans is controlled by means of these rules and regulations.Therefore, how these rules and regulations are performed is a decisive factor in achieving goals and prospects ofurban development plans. Quantity and quality of construction regulations in Tehran from the first comprehensiveplan approved in 1970 to the strategic-structural plan in 2007 was changed along with the evolution of generalurban developments and special development policies in Tehran. Also, necessity of updating rules and regulationsof urban development is considered according to lack of full performance or low performance of many of the rulesand regulations of previous plans. A major part of challenges about non-implementation of these regulations canbe studied in the form of anomalies of constructional violations. This research analyzes and evaluates the wayof performing these regulations and status of constructional violations with the goal of analyzing challenges ofperforming rules and regulations of urban development in Tehran metropolis using descriptive-analytical method.Hence, four time intervals: the interval between performing regulations of first comprehensive plan of Tehran andfinancial self-sufficiency of municipal, the interval between implementing density sales policy and modifyingregulations of Tehran, the interval between performing Amendment of planning regulations of Tehran andannouncing the rules of detailed and comprehensive plan of Tehran and after that are evaluated. Also, causes ofcreation of constructional violations and their consequences in the failure of urban development plans were analyzedand the results demonstrate that the factors such as physical field and limitations and natural tendencies of urbandevelopment, underlying society and economy of city, defects of construction rules and regulations and inefficienturban management system are the most important causes of constructional violations in Tehran metropolis.