Severe adhesion, also referred to as galling, is a critical problem in press hardening, especially in stamping tools used for hot forming of Al–Si-coated ultra-high strength steel. Galling is known to develop rapidly on the tool surface and it negatively affects the quality of the formed products. Earlier research on this topic has focused on the galling initiation. However, studies on the galling development during extended sliding and the corresponding quantitative measurement still lack depth. In the present study, a tribological test is established to study the galling development under press hardening conditions. The tribological test set-up aims to simulate extended sliding between the Al–Si-coated boron steels and the tool die material. The contact conditions in the interface are studied by a numerical model of the tribological test. The friction coefficients and material transfer are discussed taking into account the variation of the different test conditions. Using the results from the tribological tests, the galling simulation is performed in the numerical model. A geometry-updated sample based on the galling (transferred material build-up) height is simulated and the consequent pressure fluctuation is obtained in the numerical model. This contributes to the explanation of the severe transferred material accumulation during the test.