Soil moisture content below the water table is independent of atmospheric conditions. However, with soils above the water table and near-ground surface (up to depths of 6 m or more), the environmental relative humidity (RH) has a controlling influence on the soil water content. The occurrence of alternate dry and wet seasons exposes the vadose zone soils to low (during the dry period) and high (during the wet season) RH environments, affecting the soil behavior. Hence, this study examined the impact of drying and wetting cycles induced by exposing the specimens to RH of 33 and 97%, respectively, on the compressive strength behavior and moisture retention capacity of residual kaolinitic soil. Analysis of the data showed that the drying–wetting cycles had a significant impact on the moisture retention capacity of the soil than on its compressive strength.