The present study examines rubber’s capacity of improving the swell–shrink potential of expansive clays. Two rubber types of fine and coarse categories with different geometrical features were considered. The test program consisted of standard Proctor compaction and cyclic wetting–drying tests. Scanning electron microscopy (SEM) analysis was also performed to identify the soil–rubber amending mechanisms, and to observe the evolution of fabric in response to alternate wetting and drying. Cyclic wetting–drying led to the reconstruction of the soil/soil–rubber microstructure by way of inducing aggregation and cementation of the soil grains. The greater the number of applied cycles, the lower the swell–shrink features, following a monotonically decreasing trend, with the rubberized blends holding a notable advantage over the virgin soil. The tendency for reduction, however, was in favor of a larger rubber size, and more importantly the rubber’s elongated form factor; thus, predicating a rubber size/shape-dependent amending mechanism. The soil–rubber amending mechanisms were discussed in three aspects—increase in non-expansive content, frictional resistance generated as a result of soil–rubber contact, and mechanical interlocking of rubber particles and soil grains. The swell–shrink patterns/paths indicated an expansive accumulated deformation for the virgin soil, whereas the rubberized blends manifested a relatively neutral deformational state, thereby corroborating the rubber’s capacity to counteract the heave and/or settlement incurred by alternate wetting and drying.