Uncrewed and autonomous marine vessels (UMVs) challenge the underlying paradigm of maritime laws and regulations. Yet UMVs are considered essential for safer, more efficient, and more effective maritime futures. There is a fundamental challenge facing industry and regulators about how to develop and support the nascent UMV industry while maintaining the safety and risk management principles and processes in legacy laws and regulations predicated on the conventional crewed vessel. This paper, drawing upon case studies of developer and operator experiences with Australia’s maritime safety framework, argues for an “intent-based”, flexible, and collaborative approach based on developers’ and operators’ experiences. The case studies show that ad hoc and bespoke regulatory pathways, utilising exemptions and discretions under Australian national laws, although problematic in terms of regulatory consistency and capacity to deal with scale, did allow for the trialling and deployment of two small UMVs. More importantly, the ad hoc approach facilitated information exchange between industry and regulators that is generating reforms and changes at the national level. Although focused on Australia, the findings are significant for maritime futures. It reveals a dialectical approach whereby maritime nations pragmatically work through the risks, standards, and processes that balance safety with facilitating local UMV industries, and in turn, this creates a body of knowledge to inform international reform processes. It also shows the importance of documenting and reflecting on the regulatory journeys of UMV pioneers as essential for safer, more efficient, and effective maritime industries that leverage the potential benefits of automation.