As an integral part the railway network infrastructure, insulated rail joints (IRJs) electrically isolate track segments providing critical feedback to both track signaling and train position detection systems. Because of the discontinuous nature of IRJs, accumulated damage at the railhead is high. Failure modes include plastic flow of metal across joints, bolt and fishplate failures, delamination of insulated material and, as a result of rolling contact fatigue, end post and endpost surface damage. In the current investigation, microstructural changes in the vicinity of endposts of IRJs made from both surface coated and uncoated rail are investigated using techniques of optical and scanning electron microscopy. Damaged IRJs made from pearlitic head hardened rail steel are compared with head hardened rail steel laser coated with martensitic stainless steel, the latter having an increased service life. Problems associated with the surface coating are identified and approaches to further improving IRJ resistance to rolling contact fatigue suggested.