Digitalization offers the transport sector great opportunity to revolutionize the way in which it does business, enabling improved interaction with customers, the use of novel business models that span transport modes, and fine-grained control of operations in real-time. Despite the potential advantages of digitalization of fleet and infrastructure, many transport networks have been slow to embrace novel technologies; accepted thinking is that this slow response in many traditional transport settings is due to the long lifecycle of the infrastructure on which many transport networks depend, coupled with the safety-led culture that pervades the sector, but is that true? Based on the outcomes of a workshop session held as part of an industrial Continuing Professional Development (CPD) program, this paper presents an industrial perspective on the challenges posed by the digitalization of the rail network of Great Britain, with a view to stimulating debate around the common digitalization challenges facing rail and other transport modes as we move forward into the 21st century.