April 15th, 2026
From Confidential to Disc…

Have you ever finished a “quick call” with your attorney and felt like you needed just a bit more clarification? Something stronger than Google—but not quite worth another call? So what’s the next logical step?

Ask AI.

At least, that’s what the recent publicity push would have you believe. (Click here to read our recent article on the status of AI litigation in Virginia.)

It seems simple enough. Take what your lawyer said, paste it into ChatGPT, Copilot, Claude—or whatever new tool rolls off the tech assembly line next—and get a clean, easy synopsis. Right? …Right?

Not so fast.

Your attorney would strongly recommend rethinking that next step. And their concern is not rooted in jealousy or fear that “the machines are taking over.” It is grounded in something far more concrete: preserving the sanctity of attorney-client privilege.

In February 2026, a federal judge in the Southern District of New York issued a decision holding that materials generated by consumer AI tools at the prompting of a criminal defendant were not protected by either the attorney-client privilege or the attorney work-product doctrine. On its face, that conclusion is not surprising. AI tools are not attorneys, and their outputs depend heavily on user prompts and underlying data sets.

But the real issue ran deeper.

In that case, the defendant entered prompts based on his review of subpoenaed documents and conversations with counsel. He then used a consumer AI tool to generate documents that incorporated those prompts—and, implicitly, his attorney’s advice, recommendations, and related information. When the government later executed a search warrant, those AI-generated materials were among the items seized.

The question became whether those materials were entitled to protection under the attorney-client privilege.

At its core, the attorney-client privilege protects confidential communications between a client and their attorney, shielding them from compelled disclosure. Here, however, the court identified three key reasons why the AI-generated materials did not qualify:

First, the AI outputs were not communications between attorney and client; the AI tool is not an attorney.
Second, the communications were not confidential, as the AI platform’s user agreement expressly permitted the sharing of user inputs and outputs with third parties.
Third, the defendant did not consult the AI to obtain legal advice, and later sharing those materials with counsel did not retroactively render them privileged.

The court also rejected work-product protection, finding that the materials were not prepared “at the behest of counsel” and did not reveal counsel’s legal strategy.

So what does this mean in practice?

First, if you intend to use AI tools to better understand your case, discuss that with your attorney. They may have access to secure or closed AI systems—or other resources—that can help you without risking disclosure.

Second, follow your attorney’s guidance on how (and whether) to use AI in connection with your legal matter. Information entered into consumer AI platforms may become discoverable. By contrast, when attorneys use vetted tools within appropriate safeguards, privilege protections can be maintained.

Protecting that privilege—and preserving the integrity of attorney-client communications—is worth the extra step.

The case driving much of this discussion is United States v. Heppner, Case No. 25-cr-00503 (S.D.N.Y.). It will be important to watch whether AI providers revise their disclosures and whether attorneys increasingly inquire into clients’ use of AI tools.

Ultimately, this issue is about protecting the client. Attorneys seek not only to provide sound legal advice, but also to ensure that clients understand their cases and can effectively participate in their own defense. If you have questions about your business’s use of AI, including how it may affect privilege, or about the issues discussed in this article, please contact John Stacy (jstacy@setlifflaw.com) at (804) 377-1263 or Steve Setliff (ssetliff@setlifflaw.com) at (804) 377-1261.