To tackle the problem of various types of rail damage, such as rolling contact fatigue (RCF) or wear, a profound knowledge of the occurring mechanisms is necessary. This paper presents a newly developed full-scale test rig experiment that involves inserting softer pins into the rail head. These tests help deepen our understanding of shear deformation in rail steels. Furthermore, a finite element (FE) simulation approach is introduced that can be related to the test rig experiments. With these experiments, in combination with the FE simulation, valuable information regarding the plastic deformation can be obtained. This methodology allows predictions regarding a rail’s material behaviour during cyclic wheel loading. Moreover, it enables an effective and rapid qualitative material assessment, reducing the costs of expensive and time-consuming experiments.