In-Person Location: 25 W 39th Street, 9th Floor New York, NY 10018
This program argues that the profession’s compliance-model response to AI risk (policies, training, exhortation to verify) is insufficient, and that most AI ethics problems lawyers face are better understood as delegation and supervision problems. Drawing on the Sullivan & Cromwell filing, 22 NYCRR Part 161, United States v. Heppner, and NYC Bar Formal Opinion 2025-6, the session provides a practical framework for distinguishing tasks lawyers can safely delegate to AI from judgments they cannot, tiered verification guidance matched to different categories of AI-assisted work, and concrete guidance on the emerging obligation to counsel clients about AI-related privilege and confidentiality risks.
- The Failure That Should Have Been Impossible
- Sullivan & Cromwell’s April 2026 filing in In re Prince Global Holdings: roughly 40 corrupted citations in a motion before a Chief Judge, despite mandatory AI training, tracked completion, and written verification policies
- Why the compliance model’s assumption — that lawyers fail because they don’t know the rules — breaks down when the actual failure mode is that polished AI output looks good enough to skip the verification step
- The gap between the profession’s policy response and the structural conditions under which lawyers use AI
- Delegate the Task, Not the Judgment: A Practical Framework
- The delegation threshold: what AI can reliably do (manipulate text, compare documents, generate variations) versus what it cannot (exercise evaluative judgment requiring context, client knowledge, and professional responsibility)
- The “judgment words” heuristic: why prompts containing words like reasonable, appropriate, significant, best, and material delegate professional judgment the model cannot exercise, and how to restructure prompts to request options rather than conclusions
- Three-tier verification matched to delegation type: diffs for AI-edited content (Tier 1), independent sourcing for AI-generated content (Tier 2), the lawyer’s own analysis for AI-produced evaluative conclusions (Tier 3)
- The Q1 2026 sanctions data: $145,000 across six cases, one attorney suspended, one fired — and the common denominator that none had a functioning verification practice
- NY RPC 1.1(b), 3.3(a)(1), 5.1, and 22 NYCRR § 130-1.1
- Part 161 and the Disclosure Debate
- What 22 NYCRR Part 161 does: adopted March 25, 2026, effective June 1, 2026; restates the existing certification obligation under 22 NYCRR § 130-1.1 and provides a model rule individual judges may adopt, but does not create a statewide mandatory disclosure requirement
- The patchwork of individual standing orders: Illinois’s permissive posture, Florida’s mandatory certification, California’s proposed rule amendments, and hundreds of individual federal orders with varying requirements
- The informational function of disclosure: why it matters less as a compliance obligation on the filer and more as a supervision signal for the reviewer — converting an open-ended verification problem into a structured supervision task
- Standing orders versus Part 161: Part 161 establishes a floor, not a ceiling; existing judicial standing orders survive unchanged
- NY RPC 3.3(a)(1), 1.1(b), and 22 NYCRR Part 161
- When the Client Delegates to AI
- United States v. Heppner (S.D.N.Y. 2026): consumer AI conversations held unprotected by privilege or work product; what the court held, where the confidentiality reasoning falters, and why the opinion landed on a real problem
- Consumer versus commercial AI data-handling tiers: training defaults, retention periods, ownership, and the structural divide that runs across every major LLM provider
- NYC Bar Formal Opinion 2025-6: the structural problem when the client brings AI recording, transcription, or summarization tools into the attorney-client conversation, and the limits of engagement-letter remedies
- Three affirmative obligations under NY RPC 1.1(b), 1.4, and 1.6: explain AI-related privilege risks (which requires understanding them first), provide reasonable alternatives to consumer AI tools, and strengthen communication channels to reduce the gap that drives clients to AI in the first place
- The Work Nobody Checks
- The litigation bias in quality control: every sanctions case in the AI ethics coverage arose in adversarial proceedings, where opposing counsel caught the errors — but most AI-assisted legal work circulates without that scrutiny
- Transactional drafting, regulatory filings, opinion letters, and internal memoranda: the categories of legal work where AI adoption is growing fastest and external review is thinnest
- Where the three-tier verification framework strains in non-adversarial contexts: blurred tier boundaries, no second reader, and missing feedback loops
- Building verification habits for unsupervised work: routinize the check, make verification visible to yourself, distinguish verification from re-reading, and teach the habit before the pressure arrives
- Questions & Answers (As Time Permits)
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Ropes & Gray LLP
David S. Kemp is a part of the AI innovation team at the global law firm Ropes & Gray LLP, and the managing editor of Justia’s Verdict and Oyez. He has taught at Rutgers Law School, the University of California, Berkeley School of Law, and UC Law SF (formerly Hastings College of the Law). His areas of teaching include lawyering skills, professional ethics, and generative AI.