AI and Legal Malpractice: The Coverage Gap and the Anatomy of an AI-Error Claim

Alex D. Pappas, Associate | Hunton Andrews Kurth LLP

Alex D. Pappas is an associate at Hunton Andrews Kurth LLP in Washington, DC, representing corporate and individual policyholders in complex insurance coverage matters. His work spans directors and officers liability, builders’ risk, errors and omissions, commercial general liability, and representations and warranties insurance, with a dual focus on litigation and advisory work and particular attention to emerging risks tied to artificial intelligence.

• Education & Credentials

Pappas earned his JD, magna cum laude, from Georgetown University Law Center in 2020, where he served as Senior Editor of the Georgetown Environmental Law Review. He completed his BA in Political Science at the University of Michigan in 2015. Following law school, he clerked for the Honorable Charles P. Kocoras of the United States District Court for the Northern District of Illinois. He is admitted to practice in the District of Columbia, Illinois, and New York.

• Recognition & Leadership

Pappas is a recognized voice on insurance coverage for artificial intelligence and emerging risks, writing and speaking widely on the subject. He co-authors the Hunton Insurance Recovery Blog and contributes to the firm’s Policyholder’s Guide to Artificial Intelligence. As an undergraduate, he was a two-time National Debate Tournament finalist. During law school, he interned for the Honorable Beryl A. Howell, then Chief Judge of the United States District Court for the District of Columbia, and at the US Department of Justice, Civil Division.

• Professional Involvement

Pappas is a member of the Washington Urban Debate League. He presents regularly to national audiences, including the North Carolina Bar Association, Justia Connect, Lawline, and the Rossdale Group, frequently on AI and insurance coverage. His articles have appeared in Law360, Bloomberg Law, the American Bar Association, the Review of Securities & Commodities Regulation, and Risk Management Magazine.

• Experience

Pappas represents policyholders in coverage disputes across courts and arbitration forums nationwide, including matters involving eight-figure recoveries. He represented a real estate developer in an eightfigure international arbitration over builders’ risk coverage, a translation company in a precedent-setting dispute in the District of Massachusetts, and an energy client in pollution legal liability litigation. He also advises private equity firms, financial institutions, telecommunications companies, and nonprofits on coverage strategy, from placing and negotiating policies to managing claims during investigations and disputes.

Christopher F. Lyon, Founding Partner | Cohen Cunningham DeRose Higgins Lyon

Christopher F. Lyon is a Founding Partner and Co-Chair of the Professional Liability Practice at Cohen Cunningham DeRose Higgins Lyon, practicing out of New York and Marlton, New Jersey. He focuses on the representation of professionals and businesses across a wide range of professional liability matters, with particular depth in the defense and counseling of accounting and finance professionals and firms. He also represents lawyers, architects, engineers, agents, brokers, and directors and officers, and counsels corporations in commercial disputes.

• Education & Credentials

Lyon earned his J.D. from Boston University School of Law in 2013, where he served as Senior Articles Editor of the Boston University International Law Journal, competed as Swing Speaker on the Sutherland Cup Moot Court Team, and acted as Student Coach for the ABA Arbitration Competition Team. He completed his B.A. at the University of Texas at San Antonio in 2010. He is admitted in New York and New Jersey, before all four U.S. District Courts in New York, and the U.S. Court of Appeals for the Second Circuit.

• Recognition & Leadership

Lyon has been recognized as a Super Lawyers Rising Star from 2020 through 2024, rated AV-Preeminent by Martindale-Hubbell, and named to Best Lawyers in America: Ones to Watch in 2024. As a Founding Partner of the firm, he co-chairs its Professional Liability Practice. He also serves as Co-Chair of the Accountants, Fiduciaries, and Financial Professionals Committee of the Professional Liability Defense Federation for 2025, having served as Co-Vice Chair during 2024-2025.

• Professional Involvement

Lyon is a member of the Professional Liability Defense Federation, the Professional Liability Underwriting Society, and the Lawyer-Pilot’s Bar Association. He has published in the NY Litigator, The Brief, and the PLUS Journal on topics including ChatGPT misuse and sanctions and agent and broker liability and has presented on emerging risks in accounting liability and on artificial intelligence and the law.

• Experience

Lyon is well-versed in trial work, with experience entering cases as late as two weeks before trial on exposures reaching eight figures. He has secured significant results in accountant liability, including a complete reversal at the Appellate Division, First Department that narrowed the scope of accountant liability. He has obtained dismissals of multimillion-dollar claims against insurance brokers, including an $8 million and a $30 million claim, and has represented Top 50 accounting firms before the IRS, SEC, PCAOB, DOJ, and FBI, along with corporations in commercial litigation and arbitration.

SESSION 1 – The AI Risk Playbook for Insurance Leaders | 1:00pm – 2:00pm

Examine how AI exposures including bias, privacy, IP, and regulatory claims test traditional insurance lines, then learn to define AI in contracts, assess AI-specific exclusions and affirmative products, and allocate responsibility through contractual risk transfer and indemnification.

BREAK | 2:00pm – 2:10pm

SESSION 2 – Anatomy of an AI-Driven Legal Malpractice Claim | 2:10pm – 3:10pm

Trace how AI uses and misuse triggers malpractice claims, mapping duty, breach, causation, and damages onto real hallucination fact patterns. Follow the sanctions-to-malpractice pipeline from Mata v. Avianca forward and learn the verification steps that prevent exposure.