This paper discusses the spatial vulnerability in the old town of Hebron and the reasons behind poor urban continuity between the old historical town of Hebron and its urban extension. There is noticeable lack of urban continuity with the historical old town influencing urban development attempts to produce a holistic master plan for the city of Hebron on a larger scale. The research attempts to bridge the gap between the historical roots of the city and its urban extension by discussing the causes of urban vulnerability in the old town of Hebron and the resulting fragility and discontinuity of the urban extension to achieve urban sustainability. This disconnection in the urban fabric is common in historical towns due to many reasons, such as using different construction methods throughout the time, using different architectural styles and forms as a result of globalization, the change of human activities, and finally as a result of external intervention such as invasion or political conflict. This paper will shed light on these aspects, specifically the Palestinian-Israeli conflict and the influence of the power gap between Palestinian local citizens and IDF enhancements on Israeli settlers, which produced a distorted image of the urban form and function of Hebron city. The disorder and fragmentation in the urban fabric were resisted by Palestinian citizens in Hebron City on both local and national levels. In addition, many international attempts were made to enhance the local and national identity of Hebron Old Town as a non-separable part of Hebron City. Still, these attempts need to be restudied and evaluated, and the current status needs to be analyzed on an architectural and urban scale to have a better vision for the future of Hebron City.