Looking back to the Indonesia’s political reform in 1998, after more than a decade, all of the changes related to the socio-political struggles of Jakarta residents post mass riots had shaped new Jakarta’s urban habitat character. Back then, numerous real estates and properties were brutally destroyed. Citizens who were living inside of those traumatized precincts are witnesses of the vulnerability of city space. They passed through the experiences, the survivors of those riot moments, the owners of its horrific collective memories. As post mass riot’s vulnerability impacts, the ‘fortified zones’ were taking form. The existences of barricades, tall fences, barbwires, minimum openings façade, and thickblocked walls are the symbols of this vulnerability. These urban forms and structures are related to the forming of what I called Urban Fortifications. The other forms in the category are the open wide urban streets/thoroughfares inside the city and the reality of high speed access to automobiles/vehicular movements through the inner city streets compare to providing safe spaces for pedestrians. In some areas of Jakarta, such as city centers, upper level housing complexes, and com- mercial buildings, lay-down these new urban-scapes, which had left almost permanently scarred. It had formed distinctive spaces as models for the new habitat within the urban settings. It introduced spatial dialectics of the altered urban architectural components as results of the “architecture of fear’ context (spatio-temporal) in its presence. Literature and theories on this context are ones of the essentials other than basic theories on forms and urban elements. We can see the urban city frontages which are supposedly open, the building façades of phobia, or the front-back face of properties. The urban character which contains the urban morphology of safe boundaries and limits are also the entities of which provides the appropriations of changes related to the street interactions. Moreover, the main purposes of this research are to define the actual causes and detailed transformations of these specific urban areas and spaces. Another important sequential objective is to see how it finally impacts the urban habitat and its urban quality of life. The discourse analyzes the urban conditions of parts of Central and South Jakarta urban areas and other Jakarta city streets impacted by the regretful event, after a decade of (re)development and transformations. The analysis will then identify the façade changes and urban space transformations based on results of field survey sketches and documentation. Research outcomes would be a better understanding of the urban comforts and the definition of vulnerable space term within the city’s contextual plot, especially the spaces caused by riots’ or even further as results of the weak short-term urban development planning and design. These understandings would contribute to the efforts of forming better urban habitats for the city of Jakarta opposing the ‘urban fortifications’ and/or urban development flops which has destroyed the cityscapes and its livable urban scale.