The segments of pipelines under highway crossings and rail crossings require additional considerations in their design and construction due to variable loadings, limited access, and other external factors. This paper discusses the outcomes of a study carried out to investigate the potential factors that contributed to pitting corrosion resulting in pipeline failure at a road crossing section. This paper will highlight the impact of underground water containing corrosive compounds such as chlorides in the failure of pipelines. The insights derived from this research will allow engineers to select the ideal construction methodology, choose suitable coating and insulating materials and implement adequate inspection and monitoring approaches to limit the factors that contribute to threats of corrosion. This paper will also discuss the most suitable solution and recommendations to prevent these failures arising from pitting corrosion in underground highway crossing sections of pipelines.