The article presents the results of a study of the anisotropy of the under-rail base on the dynamic settlement of sections of transitional stiffness reinforced with bottomless boxes. It is proposed to model the railway track by flat elements, each of which is represented by an anisotropic plate resting on a deformable base with its own deformability parameters. Three main directions of change in the mechanical and geometric characteristics of the structure are identified: horizontal directions along the rail strands, transverse directions along the sleepers, and vertical directions down from the level of the rail head. Setting boundary conditions for individual fragments of the track structure and varying the anisotropy coefficients allows to achieve a good correspondence between the real railway track structure and its mathematical model. Graphical dependencies for the vertical displacement of points on the median surface of a flat element modeling a segment of a railway track were constructed and analyzed based on the results of determining the frequencies of natural oscillations.