Advances in technological innovation have been deployed to support autonomous or semi-autonomous vehicles in many industries. A question that remains unanswered is why very little progress has been made in remote pilotage over the past 15 years. This paper draws together theories from innovation management and the high reliability organisation literatures to shed light on this question. Using a case study of two Australian ports, we examine a business case for remote pilotage demonstrating that despite positive cost benefit models, ambiguities in benefits exist throughout the ecosystem. The discussion sheds light on unique challenges that Port executives face where it is necessary to simultaneously develop a strategy to: (1) manage the internal innovation process, and (2) manage the external consequences of the innovation by mobilizing allies, managing opponents, and converting those who are indifferent to the innovation. The main contribution of this paper is to show that any assessment of the innovation challenge facing remote pilotage and enhanced navigational assistance requires the maritime industry to ask new questions not previously considered.