**Judge Paul A

Judge Paul A. Engelmayer sits in the Southern District of New York — the federal court that's producing more AI-related case law than any other district in the country. Appointed by President Obama in 2011, Engelmayer handles complex commercial, white-collar, and civil rights cases. His courtroom operates under SDNY's evolving AI certification framework, which got a major upgrade in 2025 when the court published a model certification form for generative AI use in filings.

What practitioners need to know: SDNY's AI rules are a patchwork of court-wide guidance and individual judge requirements. Judge Engelmayer expects compliance with the court's model AI certification, independent verification of all citations, and full transparency about how filings were prepared. The district's landmark ruling in *United States v. Heppner* (2025) — where AI-generated documents were found not protected by attorney-client privilege — has raised the stakes for every attorney appearing in SDNY.

SDNY's Model AI Certification and What It Means in Judge Engelmayer's Courtroom

In August 2025, SDNY published a model certification form regarding the use of artificial intelligence in filings. Multiple judges across the district — including Judge Vernon Broderick, who formalized his version in October 2025 — now require attorneys to file this certification. The form requires counsel to disclose whether generative AI tools were used in preparing any filing and to certify that all AI-generated content was independently verified for accuracy. Judge Engelmayer's individual practices align with this framework. If you're filing before him, treat the model certification as mandatory — attach it to every substantive filing, confirm every citation through Westlaw or Lexis, and make sure your entire team understands the obligation.

The Heppner Privilege Ruling: Why Every SDNY Attorney Needs to Pay Attention

The most consequential AI ruling to come out of SDNY is *United States v. Heppner*, No. 25-cr-00503-JSR (S.D.N.Y. Oct. 28, 2025). In that case, defendant Bradley Heppner used Anthropic's Claude to input prompts about a government investigation and his legal exposure. The court ruled that AI-generated documents are not protected by attorney-client privilege or the work product doctrine. The reasoning was threefold: the AI platform is not a licensed attorney, the communications weren't confidential because the platform's privacy policy allows data collection, and the communications weren't made for the purpose of obtaining legal advice. While Judge Jed Rakoff issued this specific ruling, it applies across SDNY and directly affects how Judge Engelmayer's cases handle AI-related discovery disputes.

Judge Engelmayer's Background and Approach to Complex Cases

Before taking the bench, Engelmayer served as an Assistant U.S. Attorney in SDNY and practiced at Wilmer Cutler Pickering Hale and Dorr. He's known for meticulous written opinions and a no-nonsense approach to case management. His docket regularly includes high-profile commercial litigation, securities fraud, and constitutional claims. In January 2026, Congressman Ro Khanna sent a letter to Judge Engelmayer regarding matters before his court — a sign of the political visibility his cases carry. For attorneys, this means your filings face serious scrutiny. Sloppy AI-generated briefs with fabricated citations won't just draw sanctions — they'll destroy your credibility before a judge who reads everything carefully.

Practical Compliance Steps for Filing Before Judge Engelmayer

Step 1: Download and review SDNY's model certification form from the court website before filing. Step 2: If any generative AI tool — ChatGPT, Claude, Copilot, Harvey, or similar — was used at any stage of drafting, complete the certification honestly and attach it. Step 3: Run every single citation through a traditional legal research database. The *Heppner* ruling means AI outputs aren't just unreliable — they may be discoverable. Step 4: Establish an internal AI use policy for your team. Document which tools were used, by whom, and how outputs were verified. Step 5: Monitor SDNY's evolving rules. Individual judges update their requirements, and the court's model certification may be revised. Check Judge Engelmayer's individual rules page on the SDNY website before every filing.

How Judge Engelmayer Compares to Other SDNY Judges on AI

SDNY doesn't have a single uniform AI policy — it's a judge-by-judge system. Judge Broderick has one of the most formalized AI certification requirements. Judge Rakoff issued the landmark privilege ruling. Judge Sidney Stein and other judges have adopted variations of the model certification. Judge Engelmayer falls in the middle of this spectrum: he expects compliance with the court-wide framework and takes accuracy seriously, but hasn't issued the kind of headline-making standalone AI order that some colleagues have. Don't mistake that for lenience. SDNY as a whole is the most aggressive federal district on AI accountability, and any judge in this courthouse will hold you to that standard.

The Bottom Line: Before filing in Judge Engelmayer's courtroom, complete SDNY's model AI certification, verify every citation through traditional research tools, and build an internal documentation trail for your team's AI usage. SDNY is ground zero for AI-in-litigation case law — come prepared or don't come at all.