5th Circuit: Judge Wingate AI Errors Prompt Review of Mississippi DEI Case

• A U.S. District Judge issued a temporary restraining order in July 2025 that contained multiple factual and legal errors.
• The errors originated from a law clerk's use of Perplexity, a generative AI tool, to synthesize information for an early draft of the order.
• Even after the initial order was withdrawn and replaced, an erroneous citation, termed an "AI hallucination," persisted in the amended document.
• The 5th U.S. Circuit Court of Appeals is now reviewing whether to reassign the case due to these AI-induced errors, prompting debate over the validity of a subsequent preliminary injunction.
• This incident highlights judicial scrutiny of AI use in legal proceedings and the critical need for rigorous verification of AI-generated content.

The persistence of AI-induced errors, even after an initial correction, highlights the critical need for rigorous human oversight and verification of all AI-generated content.

The Fifth U.S. Circuit Court of Appeals in New Orleans is currently examining a significant procedural issue stemming from a district court ruling concerning a Mississippi statute. This law, House Bill 1193, which aims to prohibit programs that promote diversity, equity, and inclusion (DEI), is currently under a preliminary injunction that blocks some of its provisions. The appellate court is considering whether to reassign the underlying case after U.S. District Judge Henry T. Wingate of the Southern District of Mississippi issued an initial order riddled with inaccuracies.

In July 2025, Judge Wingate issued a temporary restraining order (TRO) that aimed to block the enforcement of the controversial Mississippi DEI law. However, this initial order contained several critical flaws. It incorrectly referenced allegations and parties who were not involved in the lawsuit, cited declarations from four individuals that did not exist, and included language that was not present in the state law being challenged. Following concerns raised by the Mississippi attorney general’s office, Judge Wingate withdrew the problematic TRO. He subsequently replaced it with a corrected version of the order.

Judge Wingate later clarified the origin of these errors, explaining that a law clerk had utilized Perplexity, a generative artificial intelligence tool, to synthesize information from the case docket. He further stated that the flawed order was an early draft that had not yet undergone the standard, multi-layered review process typically applied to judicial documents.

The procedural missteps have drawn sharp scrutiny from the appellate bench. During recent deliberations, 5th Circuit Judge Jerry Smith highlighted the gravity of the situation, particularly noting that an erroneous citation persisted even in the amended order issued by Judge Wingate. Judge Smith reportedly questioned the seriousness of such a persistent error, especially given the prior issues that led to the withdrawal of the initial order. He specifically pointed to the continued presence of what he termed an "AI hallucination" in the finally issued document, emphasizing the profound implications of such a flaw in a judicial pronouncement.

This incident underscores growing concerns within the legal community regarding the judicial use of generative AI. The fact that an AI-generated error, or "AI hallucination legal ruling," could find its way into a 5th Circuit AI court order, and even persist through an amendment, raises significant questions about the reliability and verification processes for legal documents produced with AI assistance. The 5th Circuit's current review signals a critical examination of how courts can ensure the integrity of their rulings when leveraging new technologies.

The ongoing review by the 5th Circuit involves conflicting arguments from the parties involved in the challenge to the Mississippi DEI law. Robert McDuff, an attorney representing the student groups who are challenging the state law, contended that the preliminary injunction ultimately issued in the case should remain in effect. His argument rests on the premise that Judge Wingate, not an artificial intelligence tool, made the ultimate decision, thereby validating the injunction despite the earlier procedural issues.

Conversely, Deputy Mississippi Solicitor General Anthony M. Shults urged the 5th Circuit to vacate the preliminary injunction order entirely and reassign the case to a different district court judge. Shults expressed significant concern that the preliminary injunction order did not disclaim the initial, flawed temporary restraining order. Instead, he argued, it embraced and relied upon the problematic legal reasoning contained within the original, AI-influenced TRO, thereby perpetuating its errors. The appellate court's decision on these arguments will have direct consequences for the future of the Mississippi DEI law injunction.

This case serves as a stark illustration of the potential pitfalls associated with the uncritical adoption of generative artificial intelligence in legal practice, particularly within the judiciary. The persistence of AI-induced errors, even after an initial correction, highlights the critical need for rigorous human oversight and verification of all AI-generated content. The 5th Circuit's deliberation on whether to reassign the case or vacate an order due to these Judge Wingate AI errors sets a significant precedent. It signals that courts are taking AI-related inaccuracies seriously and may challenge rulings based on such flaws.

The incident involving Judge Henry T. Wingate and the Perplexity AI tool underscores the imperative for legal professionals, including judges and their staff, to exercise extreme caution when integrating AI into their workflows. The potential for an "AI hallucination legal ruling" to undermine judicial integrity and lead to procedural challenges is a growing concern. This situation reinforces the message that while AI can be a powerful tool, it does not replace the fundamental requirement for human diligence, expertise, and a thorough review process in legal decision-making.

This case underscores the critical need for lawyers and compliance officers to rigorously verify all AI-generated content, particularly legal citations and factual assertions, to avoid severe professional repercussions and potential challenges to court filings or orders. It highlights judicial scrutiny of AI use and the potential for orders to be vacated due to AI-induced errors, setting a precedent for challenging rulings based on such flaws.

Source: Original reporting via Law.com