Capital is available. Projects exist. So why do so many maritime infrastructure and vessel investments stall between pilot and scale? This one-hour workshop moves beyond traditional financial modeling to address the real constraints blocking maritime deals – and gives participants a practical framework to diagnose and navigate them. Part 1 – the constraint landscape – why maritime deals fail: An overview of the five constraints that block scale in legacy maritime industries: stakeholder misalignment, business model gaps, regulatory uncertainty, capability deficits and public legitimacy. Illustrated with real examples from port infrastructure, autonomous vessel development and energy transition projects. Part 2 – live constraint diagnosis: Interactive exercise using an anonymized deal scenario drawn from a real maritime investment situation. Participants work through a structured diagnostic to identify the binding constraint, then discuss how the diagnosis changes the deal structure. Scenarios may include an early-stage autonomous submersible cargo platform (based on the SeaTrain concept), a port authority weighing shore power infrastructure, or a family office considering floating energy infrastructure for an island market. Part 3 – from diagnosis to deal structure + open discussion: How identifying the right constraint leads to different engagement models: phased investment, operational due diligence requirements, milestone-based capital deployment and the role of embedded operational leadership in de-risking scale-up. Open floor for participants to bring their own deal challenges.