Advances in technology have improved operator performance and efficiency in transport but it is not uncommon for end users to resist technology in spite of its benefits. Operators may resist technology from genuine and legitimate concerns though it is often seen as unjustified. While beneficial, such resistance can have detrimental effects on operations and safety, and can result in the withdrawal of a technology. Theories relating to technology acceptance include elements such as perceptions about the purpose and use of the technology, personal impact, individual characteristics, peer influence, perceived equity, and organizational factors. Although considerable research into technology acceptance and resistance has been conducted in other domains, very little has been conducted in transportation. Findings from two Australian studies are reported which examined train driver attitudes to two state-of-the-art technologies aimed at enhancing skills development and real-world decision-making. The technologies were implemented in the form of in-vehicle information support and simulated learning. Analysis of interviews defined three overarching themes relating to technology resistance: task dynamics related to ways of working and safety; redundancy regarding the utility of the technology and the impact on job security; and personal impact with respect to effects on status and the drivers’ capacity to learn new skills. It is argued that domain-specific characteristics must be considered when designing and implementing new technologies to ensure that benefits of technologies are optimised. It is also argued that resistance should be seen as a positive element of the design and implementation process. This paper has high relevance for transport researchers, and practical application for rail organisations and policy makers.