The effects of complex well conditions in shale oil wells on the swelling and tribological properties of high-acrylonitrile stator rubber used in screw pumps were investigated in this study. Tests were conducted considering the combined effects of immersion medium, temperature, and duration. The key parameters measured included mass change rate, volume change rate, hardness, elongation at break, tensile strength, surface micro-morphology of the rubber after thermal expansion and swelling, friction coefficient, and wear quantity. The results indicated that in the actual well fluids, the mass change rate of high-acrylonitrile rubber ranged from −1.08% to 1.29%, with a maximum volume change rate of 2.78%. In diesel oil, the greatest mass change rate of the rubber was 4.68%, and the volume change rate did not exceed ±1%, indicating superior swelling resistance. In both actual well fluids and diesel oil, the maximum decreases in hardness were 8.7% and 9.5%, respectively. Tensile strength and elongation at break decreased with increasing immersion temperature, with elongation at break in 80 °C diesel oil decreasing by over 50%, indicating a significant decline in the tensile properties of the rubber. The average friction coefficient of rubber specimens immersed in actual well fluids at three temperatures, as well as in diesel oil at 25 and 50 °C, decreased compared with the high-acrylonitrile rubber without thermal expansion and swelling. However, the average friction coefficient of rubber specimens immersed in diesel oil at 80 °C increased. The wear quantity of the rubber increased following immersion in both media. Additionally, the friction coefficient and wear quantity of the rubber increased with increasing immersion temperatures. The results of the study can offer valuable insights into assessing the durability of properties in high-acrylonitrile stator rubber under complex well conditions.