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Abstract Transparency is essential for public awareness of government activity and in holding officials accountable for their behavior and decisions. However, executives understandably have a desire to maintain autonomy over the flow of information outside of the executive branch, which can sometimes lead to a clash between government openness and executive control over information. This article investigates executive branch transparency along two specific dimensions: threats to the preservation of government information, and the judicial monitoring of executive branch transparency. Federal law directs executive branch actors to preserve government information. Statutes and regulations detail governing policies as well as guidelines that apply to every presidential administration. However, we consider each rule and recommendation through the lens of the Trump administration to gain greater clarity and precision. The Trump administration proves a useful focus for our empirical analysis because of its recency as well as multiple reports of its improper handling and preservation of records. We lay out and develop a typology of threats to record preservation. Preservation conflicts have emerged across multiple presidential administrations and have become increasingly common and visible. Judicial monitoring of executive branch transparency has become a crucial tool to address the withholding of records. We show that federal judges can play a vital role in defining the boundaries of government transparency through their decisions in Freedom of Information Act (FOIA) litigation. The U.S. Department of Justice oversees and often leads the government's defense against FOIA actions. We find that federal judges are most likely to require executive branch responsiveness and disclosure when the judges' underlying policy preferences are most distant from that of the administration. Our findings should inform reforms to protect government transparency.