users to experience urban spaces in a more deliberate and accurate manner, and thereby improving social interactions. The pedestrian area of Imam Hossein Square, which is an important square in Tehran, was a widely criticized project. The present study aims to investigate the environmental qualities of Imam Hossein Square physically, perceptually, and socially using behavior analysis through questionnaires and inferential statistic techniques, including regression analysis and Pearson correlation coefficient. The findings suggest that the most important factors affecting the quality of urban squares are sensory richness, consideration of human scale and pedestrian-orientedness, legibility, and safety and security. Imam Hossein Square, however, has mostly failed to meet most of the quality criteria studied. Other reasons for the relative failure of the project include insufficient planning, lack of attention to microspaces and retail stores, inappropriate management of land use after the construction of the pedestrian area, and lack of planning for social events in the square.