GIS manages urban spatial information using the isotropic model of space and Euclidean geometry, both of which are based on experience with solid bodies with determined boundaries. To model urban spatial information through Euclidean geometry means to interpret urban space as being populated with objects with determined boundaries. This chapter presents a view of urban space as an ensemble of elements and entities with uncertain boundaries. It is assumed that most of the boundaries in urban space are uncertain and undetermined per se, and that their determination depends on the context in which the elements and entities are observed. The chapter discusses some of the main artifact administrative boundaries e.g. districts, and postal, telephone service boundaries and explains religious space and holy places as belonging to administrative and territorial contexts. It provides an analysis of uncertain boundaries of physical urban artifacts and how they are perceived with respect to their functions and the processes they serve.