The aim of our current research, reflected in this article, is to come closer to creating a harmonious and sustainable system “urban resident - environment”, in this case from a geotechnical point of view. For this purpose, the concept of the sustainability resource of natural and man-made geotechnical systems can be applied. The resource of sustainability of complex natural systems to external influences means the ability of the system to maintain its appearance and basic functional features, despite these influences (Iegupov & Strizhelchik, 2021). This applies to both the natural conditions of a specific territory and complex systems, for example, the system “man - engineering and geological environment of the city”. This concept is considered to have possibilities and prospects for predicting the impact and consequences of construction on natural and engineering-geological conditions in urban areas. Several types of uncertainty arising in predicting changes in engineering and geological conditions are identified: natural uncertainty, strategic, methodological, conceptual, temporal, and parametric. Some ways of solving the emerging problems of forecasting changes in engineering-geological conditions in urban areas are proposed, in particular, ways of reducing specific types of uncertainty. A general forecasting scheme for geotechnical engineering is presented.