During the period of protracted military conflicts, significant changes are taking place in the social, humanitarian and infrastructural spheres for civilians, who find themselves in the area of military confrontation. The military conflict in eastern Ukraine began in spring 2014. Despite various efforts at the international level, a peaceful settlement of the conflict has not yet taken place. In cases of prolonged conflicts, a buffer zone is formed along the line of contact, the so-called “gray zone”. It is a kind of parallel reality of human existence in very difficult, extreme and dangerous conditions. The purpose of this article is to show how a military conflict determines the direction of urban transformation, and influences the change in the typology of public buildings and structures in the “gray zone”. The article uses a comprehensive approach based on statistical analysis, urban planning and typological analysis of open source materials. In 2014, after the signing of the Minsk Protocol, the term “gray zone” was introduced. This buffer zone corresponds to the length of the collision line and is 457 km, on either side of which there is a 30 km neutral territory. According to the Memorandum, the Cabinet of Ministers approved a list of settlements located in the “gray zone”. Weapons were separated from the demarcation line (from 8 km to 120 km) on both sides. In the “gray zone” in Donetsk and Luhansk regions, 350,000 people are estimated to be living under these difficult conditions, who face a variety of daily problems, because social settlement mechanisms are poorly functioning there. In addition, there is a significant loss of housing and infrastructure (approximately 10,000 infrastructure damage has been sustained). The most devastating settlements are located on the collision line as they are strategic points in the distribution of spheres of influence between the parties of the conflict. Within the “gray zone” are urban transformations, which are associated with the emergence of new functions: military and humanitarian. The military function is reflected in the command and observation point equipment, firing points and boundaries of the defense line, control facilities, fortifications and more. Humanitarian one envisages the emergence of territories where social, medical and humanitarian relief facilities are located. For that purpose, surviving public buildings (schools, hospitals, etc.) often change their function. Thus, it can be argued that in conditions of military confrontation, there is an “adaptation” of the existing urban situation to new needs and “re-profile” the typology of buildings, demonstrating the importance of ensuring their “flexible planning”.