Modern technologies need more mineral resources for energy generation, metallurgical products, chemicals, and many other uses. These resources are usually extracted from the Earth’s crust. Many engineering underground-space infrastructures are left after mining activity, with their very interesting features such as very large storage capacities (e.g., for hydrocarbons, hydrogen, radioactive, or other waste), and long-term geomechanical stability. Our original experiments were carried out in the conditions of an underground metal ore mine where typical mobile drilling rigs, additionally equipped with a set of sensors for recording signals as effects of rock−drill interaction were used for the research testing. A series of boreholes with diameters of Ø38 and lengths of up to 9 m in the rock medium were drilled in the “weak” and “strong” rock masses, and the frequency spectra of their signals were analyzed with the use of the fast Fourier transform (FFT) and short-time Fourier transform (STFT) algorithms. According to the proposed idealized theoretical model of the disturbance and the distinctive acceleration value of the drilling characteristic, the location of the critical discontinuities in the roof of the excavation were recognized. The most important advantage of the proposed method is the quantity and objective monitoring method for detection of a critical rock mass defect (discontinuity) that is significant for the potential functionality of underground workings as a potential energy storage room and their reinforcement.