In this paper, we have investigated the stress distribution induced by a normal load moving across an irregular micropolar layer imperfectly bonded to an orthotropic half-space under initial stress. The analysis considers a parabolic surface irregularity on the layer and an imperfect interface between the layer and half-space. Using appropriate boundary conditions and a perturbation technique closed-form mathematical expressions are derived for normal, tangential, and couple stresses. Numerical computations and graphical analyses have been conducted to illustrate the significant effects of dimensionless parameters such as frictional coefficient, irregularity depth, irregularity factor, coupling factor, bonding parameters, and initial stresses on the normal, tangential, and couple stresses. The results reveal that these characteristics significantly influence the stress distribution within both the irregular upper layer and the underlying half-space. These findings have practical implications across various fields, including highway and airport runway construction, heavy haulage, civil engineering, and earthquake engineering, where accurate stress modeling is essential for infrastructure stability and safety.