Planetary gearboxes generally consist of a ring gear, or gear body, connected with the input and output flanges by means of several screws, equally spaced along the diameter. The ring gear is manufactured with steel, whereas the flanges are usually made of cast iron. These screws must provide axial preload between the parts, allowing the assembly withstanding the breakaway torque given by the difference between the output and input torque applied to the gearbox. For a given screw geometry, the axial preload can be calculated, provided that the friction coefficients in the thread and in the underhead are known. Most often, the tightening torque is the only parameter being controlled during assembly and service operations. Hence, it is mandatory to know the friction coefficients of the joint. These depend, among others, on the hardness, roughness and texture of the mating surfaces, as well as on the lubrication state of the joint. In fact, the addition of a lubricant modifies the tribological behavior of the joint, thus the wearing evolution of the surfaces across repeated tightening operations. The present work tackles the following two aspects: (i) the characterization of the preloading force–tightening torque relationship on the actual component by means of a dedicated specimen, (ii) the evaluation of the influence of lubrication on the evolution of the frictional characteristics of the joint across several re-tightening operations. The present work has been carried out by means of both numerical finite element analyses and experimental stress analysis techniques.