Fifth Circuit takes Mississippi DEI case from judge whose orders had AI hallucinations

What the Fifth Circuit decided

A federal appeals court on 22 October 2026 vacated a Mississippi judge's order blocking the state's law against diversity, equity and inclusion programmes in public schools and universities, and directed that the case go to a different judge. In a published opinion in Jackson Federation of Teachers v. Fitch, case number 25-60496, a three-judge panel of the U.S. Court of Appeals for the Fifth Circuit said the proceedings before U.S. District Judge Henry Wingate were "a botch job, to say the least", pointing to orders that contained parties, declarations, quotations and a court case that do not exist.

The opinion was written by Circuit Judge Jerry E. Smith and joined by Judge Kurt Engelhardt. Judge Catharina Haynes concurred only in the final paragraph, which vacates the preliminary injunction, remands the case and directs the chief judge of the Southern District of Mississippi to assign it to a different district judge for all further proceedings. The practical effect is that Mississippi's House Bill 1193, passed in April 2025, is no longer blocked while the challenge continues in front of a new judge.

The case is about education policy, but the reason it drew national attention is a technology failure. Judge Wingate had acknowledged in 2025 that a law clerk used AI to help draft an early version of a temporary restraining order, and the appeals court made the hallucinated content a central part of its explanation for removing him from the case.

What went wrong in the original order

According to the opinion, the original temporary restraining order issued on 20 July 2025 named as plaintiffs eleven individuals and organisations that were never parties to the lawsuit, including a sorority chapter, a library association and a student group the court describes as "purported". It named two state officials as defendants who had not actually been sued in those roles. It claimed, without evidence in the record, that three colleges had already cancelled programmes because of the law.

It also misquoted the statute. The order described H.B. 1193 as covering "race or sex stereotyping", "race or sex scapegoating", "critical race theory" and "institutional bias", none of which appear in the act's text, and cited declarations from four people who, the panel says, do not appear anywhere in the record "and may not even exist". These are the classic signs of a language model filling gaps with plausible-sounding detail, a failure mode AI Lookout covers in its explainer on AI hallucinations.

The citation that survived the correction

Two days after the order, Mississippi's lawyers filed a motion pointing out the errors. The district court then removed the original order from the docket and replaced it with a corrected version backdated to 20 July, without explanation, and refused a request to restore the original as a superseded record. It called the mistakes "clerical". The appeals panel notes that it only has the original because the state attached a copy as an exhibit, saying it was "grateful" and "lucky" to have it.

After U.S. Senator Chuck Grassley accused the court of using AI, Judge Wingate wrote that a law clerk had used AI to help draft an earlier version that was docketed by mistake. Bloomberg Law reports the judge said last year that the tool was Perplexity. His letter argued the errors did not relate to "core legal reasoning or the ultimate judgment on the merits".

The corrected order did not fix everything. At oral argument in the Fifth Circuit, it emerged that the replacement still cited "Cousins v. School Bd. of City of Norfolk, 503 F.2d 422", supposedly a 1974 Fourth Circuit decision. The panel says the case does not exist. The reporter page it points to falls in the middle of an unrelated Sixth Circuit case, United States v. Anderson, and the pinpoint pages belong to a Second Circuit case involving Avis Rent A Car. Because the later preliminary injunction "generally incorporates by reference" the restraining order's analysis, the court said the invented case was arguably part of the injunction's reasoning too.

Why the panel took the case away

Federal appeals courts can send a case to a new judge on remand, but the Fifth Circuit calls this an "extraordinary" and "rarely invoked" power. The panel applied its two existing tests: whether the original judge would struggle to set aside views based on findings now rejected, and whether an objective observer might reasonably question the judge's impartiality.

On the first test, the court said that simply cutting the hallucinated facts out of the order, without explaining why the order should stand without them, already suggested difficulty setting those views aside. Given "the embarrassment of the AI hallucinations and mistakes of law", the panel wrote, a judge might be tempted to prove his original view correct. It added that public esteem for the judiciary would suffer if the case went back to the same judge.

The opinion is careful to say the AI problems were not the only issue. It accuses the district court of "impoverished legal analysis", of brushing aside the Supreme Court's 2024 framework in Moody v. NetChoice for facial First Amendment challenges as only "supposedly" required, and of misreading Trump v. CASA on the scope of injunctions. One line ties the two strands together: "The district court—or perhaps, being charitable, its AI agent—ignored and manipulated governing law, apparently to satisfy a policy agenda."

What the ruling says about the law itself

Most of the 28-page opinion is not about AI. It sets out how the new judge should read H.B. 1193 and which constitutional tests to apply. The panel says the law regulates public schools, colleges and educators, not students, and that it bans required diversity training and courses or offices that promote listed concepts, with exceptions for scholarly research, creative work, accreditation requirements and privately funded student groups.

The plaintiffs, represented by the ACLU of Mississippi and the Mississippi Center for Justice, found something to welcome. Courthouse News reports the center called the ruling an important development because the panel read the law as not barring classroom discussion of subjects like race or sex. Judge Haynes wrote separately that teachers must not be prevented from teaching students not to discriminate.

The opinion's legal analysis, including its views on academic freedom and a recent Eleventh Circuit decision, is likely to be contested. AI Lookout is not taking a position on the education law. The point for readers following AI is narrower: an appellate court has now cited hallucinated content in a judge's own orders as part of the reason to take a case away from that judge.

Why this matters for AI in courts

Courts have spent the past three years sanctioning lawyers for filing briefs with invented citations produced by chatbots. This case flips the direction. The errors came from inside chambers, in an order that carried the force of law and blocked a state statute for more than a year. An order like that cannot be withdrawn as easily as a lawyer's brief, and it fell to the state's lawyers to point out that people and quotations cited in it were not real.

The episode also shows how hard hallucinations are to clean up after the fact. A first correction removed the obvious invented parties but left a fabricated precedent that nobody caught until appellate argument. That matches a pattern AI Lookout has reported elsewhere, including a German court ordering Google's AI Mode to stop pinning another man's crime on a doctor: once a model's fluent but false statement lands in an authoritative document, it spreads and is hard to retract.

Generative AI is also arriving in legal work from another direction, through discovery fights over how models were trained, such as the order requiring Meta to name everyone who approved downloading pirated books for Llama. Judges are being asked to rule on AI while some of them are using it to write.

How courts and lawyers can avoid the same failure

The lesson is the one that applies to any AI-assisted research: every citation, quotation and factual claim needs to be checked against the primary record before it is relied on. In a legal setting that means pulling each cited case from a reporter or database, comparing every quotation with the statute's text, and confirming that every named party and declarant appears in the docket. AI Lookout's guide to verifying AI answers covers the same habits for everyday use.

Transparency matters too. The Fifth Circuit was clearly troubled that the original order was quietly replaced, backdated and kept off the public docket, and that the errors were described as clerical. Keeping a superseded version visible, explaining what changed and disclosing when AI tools were used in drafting would have made the problem smaller, not larger.

Retrieval tools that ground answers in real documents reduce but do not remove the risk, as the surviving Cousins citation shows. A chatbot can return a real-looking volume and page number that point to something else entirely, and only a human who opens the source will notice.

What happens next

The case now goes back to the Southern District of Mississippi, where the chief judge must assign a new judge. That judge will have to decide the challenge again under the framework the Fifth Circuit laid out, comparing the law's lawful and unlawful applications as Moody requires. The plaintiffs could also ask the full Fifth Circuit to rehear the case or seek Supreme Court review, though no such filing had been reported when AI Lookout checked on 23 October 2026.

Neither Judge Wingate's chambers nor the Mississippi attorney general's office had responded to Courthouse News by publication of its report. The opinion does not refer the judge for discipline, and it does not set any new rule on AI use by courts. Whether the ruling pushes federal courts toward formal disclosure rules for AI-assisted drafting is the open question to watch.