Metal-to-metal seals are used in connections of casing and tubing in oil and gas wells. This paper describes the mechanisms of sealing metal-to-metal seals as investigated using an experimental setup and a stochastic numerical sealing model. Experiments were conducted for a variety of thread compounds and applied pin/box surface coatings. The results were used to validate a stochastic numerical sealing model for sealability. The model couples a contact-mechanics model with a flow model and takes into account the influence of all the surface-topography features by introducing the concept of seal permeability. Once validated, the model was used together with the experimental results to better understand the sealing mechanisms of metal-to-metal seals. The sealing configuration is a face seal with an 80-mm roundoff radius on one face pressing against a flat on the other face. The face-seal specimens were manufactured from P110 tubing to ensure material properties that are representative for casing or tubing. The test setup used is designed for investigating only the metal-to-metal seal of the connection. The setup can perform rotary sliding under constant load to simulate surface changes during makeup and subsequently perform a leakage test. The sealing limit is determined by applying 700-bar fluid pressure and then gradually reducing the normal force until leakage is observed. The data are subsequently used to validate the previously published stochastic numerical sealing model. The results indicate a strong dependence on the type of thread compound used for the onset of leakage. The thread compound affects the amount of wear and thus changes the surface topography of the interacting surfaces. It is shown that the stochastic numerical sealing model is capable of predicting the onset of leakage within the experimental accuracy. The model shows further that certain surface topographical features improve the sealing performance. In particular, a surface manufactured by turning on a lathe that is in contact with, for instance, a smooth shot-blasted surface topography leads to highly localized contact areas, which in turn yield the best sealing performance.