This research explores the role of urban planning interventions in shaping urban alienation in Tehran. Despite the remarkable speed of physical growth in the metropolis of Tehran—including roads, bridges, and skyscrapers—it seems that individuals are becoming increasingly alienated from themselves, their citizens, and their surrounding environment. Urban alienation, social fragmentation, and the disconnection between individuals and their urban surroundings have emerged as fundamental challenges of modern urban life. Over the past half-century, the three urban development plans of Tehran, designed to improve the quality of urban life, have inadvertently exacerbated these issues. As the primary strategic documents guiding urban interventions, these plans, instead of bridging the gap between human (inside) and the city (outside), have intensified feelings of powerlessness and lack of control over life. It could even be argued that they have deepened the distance between individuals and their own inner selves. The present study seeks to answer the question of whether urban development plans, as strategic documents in metropolises, address the issue of urban human alienation, reflection, and problem solving. In other words, can this issue be effectively tackled through urban development plans? The research approach, alongside a review of theoretical literature, employed a qualitative methodology using the Delphi technique to conduct interviews with experts and specialists in this field. The findings reveal that the decline of public spaces (10.68%), Persistent construction and physical monotony (9.71%), Expansion of large-scale highways (8.74%). These factors have played a significant role in expanding and deepening urban human alienation and social atomization.