In expansive soil regions, engineering geological disasters frequently occur in wet-dry (WD) environments, which are inseparable from the degradation of soil shear strength and structural damage. This study attempts to assess the underlying mechanisms of shear strength degradation and micro-and mesoscale damage to expansive soil under WD cycles. Recompacted specimens were subjected to several WD cycles, then triaxial shear, nuclear magnetic resonance, and scanning electron microscopy tests were performed. Moreover, the influence of the WD cycles on the shear strength of expansive soil was evaluated. The state-of-the-art image processing and analysis techniques were combined to quantitatively investigate the evolution of the soil micro-and mesostructural characteristics. The results reveal that the deterioration of soil shear strength is primarily embodied in the initial 3 WD cycles, and is mainly due to the severe loss of cohesion (about 51.69%) during this period. Soil meso-cracks were formed under the combined effects of swelling potential and tensile stress, which mainly occurred in three stages: initiation stage (1-2 cycles); propagation stage (3-4 cycles); equilibrium stable stage (5-6 cycles). Indeed, the strength and average width of cracks were increased to varying degrees, which degraded the structural integrity of the soil. In addition, the microstructure of the soil was deeply affected by WD cycles; the total volume of pores increased significantly, the particles roundness decreased marginally, and an isotropic particles orientation was achieved as a whole with local preferential orientation (depolarization). The deterioration of shear strength of the expansive soil may be attributed to alterations in humidity, which causes the clay minerals in the soil to swell and shrink repeatedly, thereby yielding the irreversible fatigue damage of microstructure and propagation of meso-cracks. This work sheds light on the properties of shear strength evolution and mechanisms of structural damage in expansive soils in semi-arid regions.