Judge Henry Wingate's staff used AI to draft TRO with hallucinated quotes
A law clerk for Judge Henry Wingate used generative AI to draft a TRO containing fabricated quotes and inaccuracies; the order was rescinded after errors were exposed, and the incident prompted a Senate Judiciary Committee inquiry.
A federal judge's staff used Perplexity and ChatGPT to draft a TRO containing fabricated quotes and legal inaccuracies.
Key facts
- What
- A law clerk for Judge Henry Wingate used generative AI to draft a TRO containing fabricated quotes and inaccuracies; the order was rescinded after errors were exposed, and the incident prompted a Senate Judiciary Committee inquiry.
- Incident date
- Jul 20, 2025
- Who
- US District Court for the Southern District of Mississippi
- Failure mode
- Hallucination
- AI surface
- Chatbot
- Severity
- High
What happened
A law clerk for Judge Henry Wingate used Perplexity and ChatGPT to draft a temporary restraining order in the case Mississippi Association of Educators v. Board of Trustees. The order contained fabricated quotes, misnamed parties, and inaccurate state-law citations. The judge rescinded the order after the errors became public and the incident drew a Senate Judiciary Committee inquiry led by Senator Grassley.
What broke inside the model
- 01 · TriggerA user asks for a fact, a citation, or a figure.
- 02 · Model stepThe model writes a fluent, confident answer.
- 03 · Control gapNothing ties the claim back to a real source.
- 04 · FailureA fabricated fact ships as if it were verified.
- 05 · ConsequenceThe false claim reaches a customer, a court, or the public.
Confidence holds, and even spikes, as the claim detaches from any source.
The AI models produced fabricated quotes and erroneous citations that were drawn into the TRO; a human-in-the-loop review failed to identify and correct these issues before filing. The subsequent rescission and inquiry demonstrate the severity of the failure.
What it cost
Sources
- PressUS judge says he won't explain error-ridden ruling in Mississippi civil rights casereuters.com
- PressLawyers Want Answers About Mississippi Judge's Made-Up Quotesnews.bloomberglaw.com
- PressUse of Perplexity, ChatGPT behind error-ridden ordersfedscoop.com
- PressGrassley Releases Judges' Responses Owning Up to AI Use, Calls for Continued Oversight and Regulationjudiciary.senate.gov
Cite this entry
https://failureindex.ai/failures/judge-henry-wingate-staff-used-draftAI Failure Index. "Judge Henry Wingate's staff used AI to draft TRO with hallucinated quotes" (FI-0278). Realm Labs. https://failureindex.ai/failures/judge-henry-wingate-staff-used-draft (indexed Jun 5, 2026).Data fields CC-BY 4.0, prose citation permitted. Incident ID FI-0278. Full dataset at /data.
Note from Realm Labs, the Index steward
How Realm would have caught this
- Prism
- OmniGuard
- AI Detection & Response (AIDR)
A runtime layer that watches the model's internal state can flag the moment a model commits to a claim it has no support for, and hold or reroute the response before it reaches a user. Realm reads those signals in real time rather than grading the transcript after the fact.