Autonomous shipping is taking artificial intelligence to another level. Its potential and problems promise a fascinating debate. Apart from crewless vessels looming on the horizon, automated ports are also pointing the way forward. Trial operations at the Shanghai Deep Water Port reveal how both ports and ship owners are embracing digitalization. Yet is automation an environmental boon or time bomb? The need for synchronization, cyber protection, legal cover, environmental measures and enforceability all take a new dimension calling for urgent debate and action.