US v. Heppner (S.D.N.Y. 2026) no attorney-client privilege for AI chats [pdf]

Original Article ↗ Hacker News Discussion ↗

Case and Ruling Basics

  • Court held that chats with Claude in this case are not protected by attorney–client privilege or work-product doctrine.
  • Key reasons discussed:
    • No attorney involved in the AI chats.
    • AI is not a lawyer and explicitly disclaims giving legal advice.
    • Terms of service state there is no confidentiality; data may be disclosed and used for training.
    • Documents were created before being shared with counsel, so could not be “retroactively” cloaked in privilege.
  • Sharing privileged attorney advice with the AI may itself waive privilege over the original communications.

Attorney–Client Privilege vs AI Tools

  • One side: AI chats are like talking to a non-lawyer friend; no privilege, by definition.
  • Other side: for many users, AI is effectively used as legal research or note-taking, and privilege should focus on case preparation, not the formal status of the “listener.”
  • Dispute over whether privilege should evolve to treat certain AI tools as part of the privileged workflow.

Comparisons to Email, Docs, and Phone Calls

  • Many note tension between this ruling and everyday use of Gmail/Outlook/Google Docs/Office 365, whose TOS also allow some data access.
  • Some argue: using cloud tools doesn’t normally destroy privilege; users reasonably expect confidentiality (similar to phone carriers as “common carriers”).
  • Others point out: this judge leaned heavily on the AI provider’s explicit “no confidentiality” language, which could equally threaten privilege for cloud-integrated tools with AI features.

Work Product and Client Notes

  • Debate over whether client-created materials for eventual use by counsel should be protected.
  • One view: only materials prepared by or at direction of counsel qualify; this decision narrows work-product and overrules a more expansive prior case.
  • Another view: strategy notes and research done by an accused in anticipation of litigation should be protected, even without explicit attorney direction.

Implications for Lawyers and Pro Se Litigants

  • Concern that pro se defendants effectively lose confidential preparation if AI use is discoverable, while lawyers may still gain some work-product protection.
  • Worry that ubiquitous AI integrations (Copilot, Gemini sidebars, etc.) could silently undermine privilege for both lawyers and clients.

Privacy Policies, Logging, and Alternatives

  • Heavy emphasis on AI privacy policies: training use and disclosure to authorities undermine any “reasonable expectation of confidentiality.”
  • Discussion of “no-log” or self-hosted models, VPN use, and even darknet-style AI services; others note legal compulsion can force logging or disclosure anyway.
  • Open question whether a HIPAA-like regime or enclave-based “legal AI” service could eventually satisfy courts’ confidentiality expectations.