In the current mine surveying practice, when assessing the harmful impact of underground construction on the earth's surface and undermined objects, the geotechnical system underground structure – rock mass is traditionally considered, which does not include the surface infrastructure. Such an approach can lead to distorted estimates of load levels, impacts and potential deformations for both buildings and the earth's surface. In order to determine the influence of the building and assess the interaction of elements of the geotechnical system tunnel – rock mass – building, the study analyses the undermining of the historical stage building of the Mariinskii Theatre by a complex of workings in Saint Petersburg metro station Teatralnaya. Numerical simulation by the finite element method in the PLAXIS 3D software package is used, the geotechnical model is calibrated in accordance with data of the field mine surveying and geodetic measurements. The models show that during undermining of buildings, their heterogeneous structure, weight and spatial rigidity significantly affect the distribution of deformations in the base of the construction, which is confirmed by localization of cracks in load-carrying structures that appeared after the start of mining operations. When assessing and predicting deformations by numerical methods, it is not always sufficient to simulate the rock mass – tunnel system, since this can lead to overestimated predicted values of the earth’s surface deformations, underestimated values of subsidence, and an incorrect assessment of the harmful effect on the undermined object. It was concluded that only an integrated approach using simulation, field measurements and survey data can ensure a correct analysis of the interaction of the rock mass, underground structures and above-ground infrastructure facilities with complex spatial geometry and allow a reliable assessment of the harmful effect on the undermined object with reference to structural damage. This contributes to adoption of adequate and timely protection measures for buildings and structures.