Defensible AI Use in Litigation: Verification Workflows and Firmwide Supervision

Sherilyn Pastor, Partner | McCarter & English, LLP

Sherilyn Pastor is a partner at McCarter & English, LLP, practicing from the firm’s Newark and New York offices, where she represents corporate policyholders in insurance recovery litigation and counseling. A trial attorney, she has recovered billions of dollars for policyholders in complex, high-value coverage matters in the United States and abroad, and she led McCarter’s Insurance Recovery Group as Practice Leader for twenty years. Beyond the courtroom, she counsels clients on risk assessment, the adequacy of their insurance programs, new insurance products, and coverage questions arising in corporate transactions.

• Education & Credentials

She earned her JD magna cum laude from Seton Hall University School of Law in 1988 and her BA cum laude from Seton Hall University in 1985. Following law school, she served as Judicial Law Clerk to the Hon. David Landau of the New Jersey Superior Court, Appellate Division, from 1988 to 1989. She is admitted in New Jersey and New York, and before the U.S. Court of Appeals for the Second, Third, and Seventh Circuits, the U.S. District Court for the District of New Jersey, and the U.S. District Courts for the Eastern and Southern Districts of New York.

• Recognition & Leadership

She has been listed in The Best Lawyers in America for Insurance Law and Litigation in New Jersey from 2015 through 2026, and named Lawyer of the Year for Litigation–Insurance in New Jersey in 2018, 2023, and 2025. Chambers USA has ranked her in Band 1 for Litigation: Insurance in New Jersey from 2011 through 2026 and recognized her nationwide for Insurance: Dispute Resolution: Policyholder for 20252026. Additional honors include New Jersey Super Lawyer from 2005 through 2025, Women In The Law by Best Lawyers in 2022, NJBIZ Leaders in Law in 2022, NJBIZ Best 50 Women in Business in 2010, Essex County’s Top Lawyers for Insurance in 2022–2023, listing in The International Who’s Who of Insurance & Reinsurance Lawyers from 2010 to the present, a Martindale-Hubbell AV Preeminent rating of 5.0 out of 5, recognition as an Insurance Trailblazer by The National Law Journal, and the Emmanuel Cancer Foundation’s Humanitarian of the Year Award in 2020.

• Professional Involvement

She is Immediate Past President of the American College of Coverage Counsel, having served as President from 2020 to 2021, Secretary/Treasurer from 2018 to 2019, and on the Board of Regents and Executive Committee from 2015 to 2018. Within the American Bar Association she is Co-Chair of the Corporate Counsel Committee for 2025–2027 and is Past Chair, policyholder side, of the Litigation Section’s Insurance Coverage Litigation Committee, which she chaired from 2009 to 2012 and co-chaired from 2012 to 2015; she has also co-chaired the Trial Evidence Committee and the Trial Practice Committee. She served on the New Jersey Supreme Court’s Professional Responsibility Rules Committee from 2002 to 2016 and on that Court’s Working Group on Ethical Issues Involving Metadata in Electronic Documents, and she is a Fellow of the American Bar Foundation. Her editorial service includes Law360: Insurance as an Editorial Consultant, the Insurance Coverage Law Bulletin editorial board since 2004, and the Appleman on Insurance Editorial & Advisory Board from 2006 to 2015. She currently co-chairs the Essex County Bar Association’s Insurance Law Committee. She speaks frequently on coverage, ethics, and emerging risk, including programs on law firm risk management responses that can jeopardize coverage, the cyber war exclusion, and navigating the generative AI frontier.

• Experience

Her results include a $15.6 million unanimous jury award for Wakefern Food Corp. against its former insurance consultants for improper advice on a property insurance policy deductible, following $4.7 million in awards against Wakefern’s insurer, and a summary judgment win establishing under New Jersey law that physical damage in a property and business interruption policy includes loss of use, value, and function. She obtained summary judgment for an industrial shelving manufacturer by persuading a federal court that a former employee’s bill padding and kickback scheme was a direct and covered loss under a crime insurance policy, and she secured complete victory for Transamerica Corporation in a dispute with a former subsidiary over $1.5 billion in coverage, where the court held after a six-month trial that Transamerica’s risk management department was not its subsidiaries’ de facto insurer. She argued for amici curiae in a cyber insurance recovery claim for a multinational pharmaceutical company, convincing the Appellate Division that an all-risk property policy’s war exclusion did not reach a cyberattack on a nonmilitary company, requiring insurers to pay $1.4 billion. She also argued Century 21 Department Stores’ COVID coverage appeal before the First Department, seeking $200 million in business interruption coverage across thirteen stores.

Jeffrey J. Cunningham, Founding Partner | Cohen Cunningham DeRose Higgins Lyon

Jeffrey J. Cunningham is a founding partner of Cohen Cunningham DeRose Higgins Lyon, serves as the firm’s General Counsel, and cochairs its Professional Liability practice from the New York and Stamford offices. He defends lawyers and other industry professionals in professional liability, ethics, and professional disciplinary matters, and acts as outside General Counsel to small and mid-sized law firms across the United States. His approach emphasizes simple systems of risk management, protecting clients before problems occur rather than only after a claim lands.

• Education & Credentials

He earned his J.D. from Fordham University School of Law in 2010, where he was an Associate Editor of the Fordham Journal of Corporate & Financial Law and received the Archibald R. Murray Public Service Award magna cum laude for pro bono work. He was a Fulbright Scholar at Philipps-Universität Marburg in 2005 and holds a B.A. from The Citadel, The Military College of South Carolina, awarded in 2004. He is admitted in New York and Connecticut, and before the U.S. District Courts for the Eastern and Southern Districts of New York, the U.S. District Court for the District of Connecticut, and the Mashantucket Pequot Tribal Court.

• Recognition & Leadership

He has been selected to New York Metro Super Lawyers for Professional Liability: Defense in 2023 and 2024, and was named a New York Metro Super Lawyers Rising Star in the same field from 2014 through 2021. He holds a Martindale-Hubbell Peer Review Rating of AV Preeminent. At The Citadel he served as a Cadet Second Lieutenant and Platoon Leader, as the First Battalion Honor Court Representative, and as Editor-in-Chief of The Brigadier newspaper.

• Professional Involvement

He is a member of the New York City Bar Association, The Cardozo Society, the Professional Liability Defense Federation, and the American Association of Jewish Lawyers and Jurists. A frequent teacher, he presents dozens of Continuing Legal Education courses each year on law firm risk management and ethics. He reaches an audience of more than 30,000 followers on LinkedIn and other platforms through a weekly newsletter on ethics and malpractice, a monthly law firm risk management newsletter, and the daily blog Point One: A Bite of Ethics a Day Keeps Legal Malpractice Claims Away, along with the Model-Rule-Meme-A-Day showcase built on the ABA Model Rules of Professional Conduct. His writing includes The Ethics of Accepting Advanced Legal Fees in Crypto in Law360 in December 2023, co-authored pieces on COVID-19 liability waivers in Fixed Ops Magazine and Risk Management in July 2020, and recent posts on law firm AI use including 10 Simple Steps Law Firms Can Employ to Safely Use AI and From AI Rule to AI Readiness: A Flat-Fee Solution for Law Firms.

• Experience

He brings fifteen years of large firm experience to the defense of professional liability cases on behalf of lawyers, law firms, and a range of other professionals, and he serves as outside General Counsel to numerous small and mid-sized law firms. His practice spans professional liability, insurance services, business and commercial litigation, and construction defect and construction worksite litigation. He gained early litigation experience as a legal intern with the Queens District Attorney’s Office and with the U.S. Attorney’s Office for the Southern District of New York, Criminal Division. He also studied law across Europe and in Israel, drawing on fluency in German, Yiddish, and Hebrew.

SESSION 1 – Malpractice Coverage for AI Risks: Exclusions, Sub-Limits, and Traps | 12:00pm – 1:00pm

This session examines how the rollout of AI-specific exclusionary endorsements is reshaping lawyers professional liability coverage, creating potential gaps in coverage under LPL and cyber policies for AI-driven malpractice claims. Attorneys will learn to identify absolute and limited AI exclusions, understand how traditional policy provisions and exclusion treat AI claims, and navigate the underwriting applications. By the end of the session, attendees will be able to audit their own policy at renewal, answer insurer AI-use questions, and evaluate emerging affirmative AI coverage products available to them.

BREAK | 1:00pm – 1:10pm

SESSION 2 – Anatomy of an AI-Driven Legal Malpractice Claim | 1:10pm – 2:10pm

This session examines how a lawyer’s use, or misuse, of AI can evolve from a routine workflow decision into a professional liability claim. The program traces a hypothetical claim from intake through discovery, focusing on failures involving competence, confidentiality, supervision, verification, client communication, and billing. Attendees will learn how plaintiffs’ counsel, insurers, disciplinary authorities, and courts may evaluate AI-related conduct and the records created by AI systems. The session concludes with practical safeguards law firms can implement to reduce risk and build a defensible AI-use framework.