The rapid advancement of Maritime Autonomous Surface Ships (MASS) is reshaping the global maritime industry, transforming shipboard operations ranging from navigation and collision avoidance to communications and propulsion. Recent milestones demonstrate how autonomous and remotely operated vessels are moving from experimental concepts to real-world deployment. Landmark voyages—including the 1,027-nautical-mile autonomous journey of the Nellie Bly using technology from Sea Machines Robotics, and the transoceanic LNG carrier Prism Courage voyage overseen by American Bureau of Shipping—highlight growing confidence in these systems. Government agencies are also embracing autonomy, with National Oceanic and Atmospheric Administration deploying uncrewed vessels for hurricane research and ocean data collection, and the U.S. Coast Guard integrating autonomous systems into its Force Design 2028 strategy. Despite rapid progress, regulatory, safety, and cybersecurity challenges remain. Classification societies such as DNV and the International Maritime Organization are developing frameworks to ensure autonomous ships meet or exceed conventional safety standards, while maintaining a requirement for human oversight. Together, these developments signal a transformative but carefully managed transition toward autonomy at sea.