Second Circuit

The Second Circuit is ground zero for AI disclosure litigation in federal courts. It doesn't have a circuit-wide mandatory disclosure rule, but the Southern District of New York — the busiest federal trial court in the country — has produced some of the most significant AI-related rulings, including Judge Rakoff's privilege ruling in Heppner that sent shockwaves through BigLaw.

With Connecticut, New York, and Vermont under its umbrella, the Second Circuit's real story plays out at the district level. SDNY and EDNY judges have been among the most proactive in the nation on AI disclosure, and practitioners filing here need to treat AI compliance as non-negotiable.

Second Circuit's Approach to AI Regulation

The Second Circuit Court of Appeals hasn't adopted a circuit-level AI disclosure mandate. But given the volume and significance of AI-related rulings coming out of its district courts — particularly SDNY — it wouldn't be surprising to see the circuit weigh in through an advisory opinion or local rule amendment in the near future. The circuit's appellate judges have shown awareness of AI issues in oral arguments, and at least two circuit judges have referenced AI tools in published opinions discussing attorney competence standards.

SDNY: Judge Rakoff and the Heppner Privilege Ruling

The most consequential AI ruling in the Second Circuit is Judge Jed Rakoff's decision in Heppner, which addressed whether communications between attorneys and AI tools are protected by attorney-client privilege. Rakoff's analysis concluded that AI-generated legal analysis doesn't constitute a privileged communication in the traditional sense, because there's no human attorney on the other end of the conversation. This ruling has massive implications for law firms using AI for case strategy — if your AI research workflow isn't structured properly, opposing counsel could potentially access it in discovery. Managing partners need to architect their AI workflows with privilege preservation in mind.

EDNY and District-Level Standing Orders

The Eastern District of New York has been nearly as active as SDNY on AI disclosure. Multiple EDNY judges have adopted standing orders requiring attorneys to certify whether generative AI was used in preparing filings. The district's chief judge issued guidance encouraging all EDNY judges to address AI use in their individual practice rules. Connecticut's district court has been quieter, with only a few judges adding AI language to case management orders. Vermont's single-judge district has addressed AI informally but hasn't adopted formal requirements.

Notable Cases and Judicial Commentary

Beyond Heppner, SDNY has produced several notable orders addressing AI in litigation. Judges have ordered supplemental briefing when they suspected AI-generated content, and at least three SDNY judges have imposed show-cause orders requiring attorneys to explain their AI usage after identifying questionable citations. The pattern is clear: SDNY judges are actively looking for AI-generated content and aren't hesitant to call it out. One magistrate judge described AI-hallucinated citations as 'the modern equivalent of fabricating evidence' during a sanctions hearing — a framing that should alarm every litigator filing in this district.

Compliance Strategy for Second Circuit Filings

For practitioners in the Second Circuit, here's the playbook: First, treat SDNY as requiring full AI disclosure regardless of whether your specific judge has a standing order — the culture of the courthouse demands it. Second, structure your AI research workflows to preserve privilege in light of the Heppner ruling — this means keeping AI analysis separate from privileged attorney work product. Third, implement dual-verification for all citations in SDNY and EDNY filings, where a second attorney independently confirms every case reference. Fourth, maintain an audit trail showing when and how AI tools were used, because judges in this district will ask. Fifth, watch for the EDNY's expected district-wide AI policy, which could become a model for other districts nationally.

The Bottom Line: The Second Circuit doesn't have a mandatory circuit-wide AI disclosure rule, but SDNY's aggressive judicial posture — highlighted by Judge Rakoff's Heppner privilege ruling — makes it the highest-risk circuit for AI compliance failures. If you're filing in New York federal courts, disclose everything and verify everything.