This conference report summarizes the key points and discussions of plenary sessions at CIGI and Oliver Wyman’s sixth annual Financial Regulatory Outlook Conference, held in Rome on November 26, 2019. Many other bilateral exchanges were no doubt sparked during and outside of the conference. Looking ahead, addressing the challenges stemming from digitalization will continue to be a major theme in the financial sector. Digitalization will continue to have implications for supervisors and regulators to consider. The first part of this conference report gives an overview of the main changes affecting financial institutions as a result of the digital revolution, inspired by the conference’s first panel. The second part focuses on the specific challenges for regulation and supervision in the new financial ecosystem. Finally, these issues are then revisited through a private sector lens, informed by the conference’s “chat rooms” (restricted seminars behind closed doors that were open to the conference participants) and subsequent panel discussion that brought together policy makers and representatives from banks and fintech companies.