Urban Design theoretical dreams and objectives seem to continuously turn out as a disappointment in many cities. Observing the urban design product -especially Cairo- triggered the research's main question; How come the city lacks the basic urban design principles of livability, legibility, walkability, and other urban design principles? This question requires investigating the process of urban design itself and how it connects to planning. If a factory is to produce cars, and the product is found to be a 4-wheeled bicycle instead, we should not blame it on the bicycle, we should examine the entire process that led to such a product, to identify what went wrong? Similarly, if a city seeks to produce an urban design product and it turned out to be something different, and noticeably inefficient, then something should be wrong with the process taken to create such a product. A thorough investigation must come in order, to perceive such a gap. The conducted research aims to identifysuch a gap in the Urban Design Process and provides answers to several questions regarding the urban design process. The Book is based on an MSc thesis conducted at Ain Shams University, Cairo, Egypt.