The process of mentoring has been recognised as an extremely valuable part of the training and learning dynamic in operational environments. However, the design of training in the rail and mining industries is extremely underserved in the area of mentoring in comparison with other domains. As two distributed industries that have extreme synergies at the sharp end, mentoring may help overcome the shortage of skilled and experienced workers in these domains in Australia. This paper outlines an argument for mentoring in the rail and mining sector, specifically as a strategy that may enhance the learning experience for the train driving and haul truck operation tasks where simulator-based training has been well established in varying degrees of sophistication. First, it provides an overview of the basic elements that underlie the knowledge requirements and core competencies of training for the train driver and haul truck operator. This is followed by a profile of the two tasks, a breakdown of the specific features of these environments that make them particularly responsive to a mentoring approach, and a review of existing simulator capabilities in these areas. The remainder of the paper draws on various theories to provide a position statement on mentoring and learning research with excerpts from case studies carried out with train drivers, haul truck operators, and trainers in both modes that support the argument. The paper concludes with an erudite discussion of how mentoring could be put into action in these industries, and how the concept may encourage a new human dimension in simulation, for thinking and research by communities of practice.