The present paper addresses how the commonly used Hertz formulas for contact stresses underestimate the actual stresses seen in practice due to temperature differentials, misalignments and other contruction-related defects. First, two failure cases of Swedish bridge roller bearings are analyzed and discussed; then, a detailed finite element (FE) model is used to investigate the accuracy of the traditional roller bearing design rules in view of issues such as abutment and girder deformability, misalignment imperfections and material nonlinearity. The bearing capacity of the studied rollers as provided by the manufacturer is used as reference. A rigorous FE model that accurately models girder, roller assembly and abutment provides the necessary information for the assessment of the related contact stresses, which were traditionally calculated by means of the Hertz analytical formulas. Numerical results first establish that roller bearings develop contact stress concentrations at the outer edges of the cylindrical drums. Second, it is established that the contact stresses are very sensitive to misalignment imperfections between the bridge girder and the abutment. Last, it is shown that the roller bearings develop inelastic deformation at relatively low loads in relation to the design load. These reasons, combined with the unlikelihood for roller bearings to shake-down, constitute the basis of the observed roller bearing failures.