Offshore megaprojects today are being executed under conditions that test the limits of coordination, safety, and efficiency. Planning can be enhanced through digital twins and integrated interface management, as evidenced by 24 vessels operating simultaneously in Buzios 7 with zero incidents. A five-year digital transformation journey across 12 FPSOs demonstrates how predictive asset management evolved from basic anomaly detection to AI-augmented decision support, saving millions while simplifying complex diagnostics. Petrobras presents a controlled-risk approach to flow assurance, operational excellence, and reservoir characterization to expand operational flexibility while reducing costs. Finally, ExxonMobil’s Payara project in Guyana showcases how regulatory adaptation, remote collaboration, and HSE innovations enabled first oil at an industry-leading pace despite the global COVID-19 pandemic. Together, these case studies demonstrate how offshore projects can be executed smarter, faster, and safer by embracing digital tools and bold strategies in the face of extreme conditions.