This interdisciplinary project, conducted using doctrinal and empirical methodologies, investigates the perennial question of why commercial shipping has been unable to digitalise. It explores how trust issues have prevented commercial shipping from digitalising, what is the role of trust in digitalisation and whether the adoption of trust-disrupting technology and digital trust legislation can help commercial shipping overcome this hurdle. New technologies, including 3D printing, 5G, AI, blockchain, cloud computing, DLT, IoT, oracles, robotics and smart contracts, will feature in the discussion. The thesis combines insights from the disciplines of law, computer science, social science and business studies to resolve the trust problem in a way that seeks to best manage the risks of digitalisation.