Although the Trump administration has sought to create a more business-friendly environment, the implications of the White House’s rhetoric for private funds remain nuanced and complex. Nearly a decade after the financial crisis of 2008, sensitivity to potential securities laws violations runs so high that the SEC continues to refine its approach to examinations and enforcement in the financial sector. Corporate executives who may not have had direct responsibility for enforcing internal compliance policies are finding their roles, and potential liability, in flux. When violations occur, chief compliance officers may find themselves on the hook even if they have tried to warn management of compliance deficiencies and failures and even if they had no analogous liability in the past. These stiffer standards and toughened scrutiny arise from the SEC’s continuing concern with protecting retail investors who may lack the sophistication that large institutional investors can employ when assessing new products. Given that evolving technologies pose unprecedented compliance vulnerabilities, the SEC is also heavily focused on cybersecurity, taking a global perspective that encompasses firms and activities far beyond the agency’s theoretical jurisdiction. All these themes came across in the annual report for fiscal year 2017 issued by the SEC’s Division of Enforcement. This article analyzes the report, along with insights from legal professionals with expertise in SEC enforcement matters. For analysis of the SEC’s stance under the new administration, see “SEC Urges Advisers Relying Upon Unibanco No-Action Letters to Submit Certain Documentation” (Apr. 20, 2017); and “Acting SEC Chair Emphasizes Agency Will Protect the ‘Forgotten Investor’” (Mar. 2, 2017).