In this episode of Behavior and Risk, we discuss Singapore’s Monetary Authority imposing collective fines totaling $21.5M on nine financial institutions—including UBS, Citibank, and Julius Baer—tied to a 2023 money laundering case involving more than $2.2B in illicit assets, the second-largest collective penalty in Singapore’s history. We recap how authorities detected suspicious networks in 2021, investigated through 2022, and executed island-wide raids on August 15, 2023 with over 400 officers, arresting nine men and one woman and seizing nearly 100 properties, 50 luxury vehicles, cash, bank accounts, and luxury goods, with total seizures later exceeding $2B. The conversation focuses on why penalties and jail terms (13–17 months for the foreign nationals) seemed low, and how the absence of charges against senior bank leadership shifts the interpretation from corruption to negligence and poor risk management. We examine MAS findings that breaches stemmed from inconsistent implementation of existing controls, including failures to conduct general money laundering risk assessments for new clients, validate sources of wealth for high-risk customers, and properly escalate concerns. We connect the breakdown to behavioral and organizational factors such as overconfidence fueled by Singapore’s reputation, automation bias, check-the-box compliance culture, loss aversion, normalization from competitors onboarding the same clients, and challenges of enforcing enterprise-wide standards across global organizations, emphasizing the gap between documented protocols and real execution—“failing to put the E in ERM,” including execution itself.