Since the tragedy of May 1998 riot in Jakarta, there have been attempts by the community to protect themselves and their properties. The efforts to add protections are achieved through fortification of the area where they live, so that it is closed and difficult to access for outsiders other than the residents. This fortification effort is against the 21st principle of The Charter of New Urbanism that encourages urban areas to be more open, letting cities become friendly places for people, inclusive, and more enliven. This principle aims to create a more dynamic contestation  in urban spaces as an effort to improve the livelihood of the city residents, and yet fortification as a protective effort is contradicting the very principle. The Kayu Putih area is chosen as the study area because the author has been part of the residents of the area and witness the development of the fortifications from May 1998 incident up till now, the period of Covid-19 pandemic. Therefore, this study reviews how the fortifications affect the contestation of spaces  within the urban setting, and sees its impact on its society . This research uses qualitative method by carrying out field surveys ethnographically in order to access the phenomena and see the impacts that come up. In addition, supporting questionnaires are used to see residents’ opinions on fortification, spatial use patterns, and the impact of fortification from time to time on their daily activities and towards the urban space. This study found interesting patterns, especially on the surrounding gates, which became sort of fortresses of the compound/area. Even though the gates closed or have limited access, its existence opens other opportunities for activities, which will not appear if the gates remain open. This research hopefully helps urban designers to consider the expected security , as well as the social aspects of fortification and its openness, so that there would be balances between the fortification effort and the contestation of its urban space.