This study aims at investigating the influence of moisture conditions on interface shear behavior of element-grouted anchor specimens embedded in clayey soils. The tests involved comparatively short embedment lengths and a device that was specially designed to facilitate moisture conditioning. Rapidly loaded pullout tests as well as pullout tests under sustained (creep) loading were conducted to characterize both the short-term and long-term ultimate shear strength of anchor–soil interfaces. Both values of the interface shear strength were found to decrease exponentially with increasing moisture content values, although their ratio was found to show a linearly decreasing trend with increasing moisture content. The interface shear creep response under pullout conditions was characterized by a rheological hybrid model that could be calibrated using experimental measurements obtained under increasing stress levels. The accuracy of the hybrid model was examined by evaluating the stress-dependent prediction model as well as its governing parameters. This investigation uncovers the coupled impact of soil moisture condition and external stress state on the time-dependent performance of grouted anchors embedded in clayey soils by correlating the interface shear strength with soil moisture content and associating the creep model with stress levels applied to the grout–soil interface.