Subsiding soils are structurally unstable and are common and Russia (Northern Caucasus, Western Siberia, etc.) as well as worldwide (China, Mongolia, Central Asia, North America, etc.). Construction and operation of buildings and structures on such soils are associated with the nonuniform subsiding of soil due to water saturation, which causes excessive deformations in basements and foundations. The geotechnical and technogenic conditions of Eastern Donbass feature the commonness of subsiding loess soils and undermining of industrial areas prone to waterlogging. The three mentioned factors have a negative impact on ground facilities due to nonuniform vertical and horizontal deformations of the Earth’s surface. Despite considerable scientific progress in studying the surficial deformations attributable to various factors, the concurrent effects of undermining, technogenic waterlogging, and manifestation of subsiding properties on the condition of buildings and structures are currently understudied. This paper proposes a method for predicting the deformation of subsiding massifs in the undermined areas of Eastern Donbass. The research team has developed an analytical method for assessing the damage to a typical urban structure simultaneously exposed to soil subsidence and undermining.