The paper examines the mechanics and physics of granular material responses at the macroscopic and microscopic levels during both monotonic and cyclic loadings. A numerical analysis referring to a long retaining wall is conducted using a two-dimensional discrete element model representing a granular system with a free top surface. On one of the lateral boundaries referring to the retaining wall, both active and passive loadings were applied monotonically as well as cyclically. First, the development of sheared zones and classic failure wedges resulting from active and passive monotonic displacements are discussed with respect to Rankine’s and Roscoe’s solution angles. Then, a series of loading cycles were performed using slow small-amplitude displacements at different stress states chosen before the occurrence of failure along the passive monotonic stress response curve. Particular interest is focused on the ultimate asymptotic cyclic response of the granular system, the occurrence of a high-mobility (convective) zone and a detailed macroscopic and microscopic analysis. Finally, major kinematical features that are displayed during cyclic loading from different starting stresses to eventually reach the same asymptotic state were elucidated through particle vortex-like flux formations, including contact rotations. The change in material stiffness was also investigated based on the evolution of strong and weak contact networks, together with the analysis of fabric anisotropy within the entire domain, including the high-mobility zone considered separately.