In order to explore the rules for the variation in the adfreeze shear strength at the interface between frozen soil and a pile foundation, and their influencing factors, a measuring system was developed to estimate the freezing strength at the interface by utilizing a pile-pressing method under a cryogenic environment. Experimental results demonstrate that the maximum vertical pressure on the pile top increased significantly with the decrease in temperature under the same moisture content. The shear stress-shear displacement curves, at the bottom part of the interface, presented strain-softening characteristics, while the strain-hardening phenomenon was observed at the upper part of the interface. The strength parameters of the interface decreased with the increase in the pile depth. Moreover, the influence of temperature on the shear strength of the interface was more significant compared with that of the moisture content. The research results can provide references for the construction of pile foundations, structural design optimization, and for frozen damage prevention and treatment in permafrost regions.