The purpose of this research work is to develop scientific approaches to solving the problem of increasing the sustainability of urbanised territories through flexible regulation of the groundwater regime. The development of a management solution for flexible regulation is carried out on the basis of the application of methods for solving problems of incorrectness.Materials for the study were data from the study of dangerous hydrogeological processes, systematised, among other matters, based on the results of monitoring natural emergencies at the Research Institute for Civil Defense and Emergency Situations. The approach proposed by the authors is based on the application of a set of methods, including methods of: system analysis, forecasting, numerical modeling, followed by the development of an optimal management solution of emergency situations at the municipal level.As a result of the numerical modeling carried out in the work, the variants of drainage systems and their operating mode are determined within the framework of the implementation of the proposed approach in the simulation mode. This makes it possible to increase the level o f environmental safety of historically developed built‐up areas, including mountainous ones.The article presents a new approach to managing the risk of emergencies in case of flooding of buildings and structures in built‐up mountainous territories, including historical territories. In such territories, the watered soil preserves the cultural layer, which determines the need for flexible regulation of the groundwater regime. The results of the study are used in carrying out research work of the State Research Institute of the Russian Academy of Sciences (GOChS) on the study of dangerous hydrogeological processes and their impact on the environment, life safety, stability of the functioning of economic facilities, monitoring and forecasting of natural emergencies.