The U.S. Department of Justice this month filed a motion arguing that conversations between a criminal defendant and Anthropic's Claude AI assistant do not qualify for attorney-client privilege protection. The February 6 filing in United States v. Heppner establishes legal boundaries for AI tool usage that could affect how professionals across marketing, technology, and other sectors interact with artificial intelligence platforms.

Bradley Heppner, charged with securities fraud and related offenses in the Southern District of New York, created approximately 31 documents by querying Claude about his legal situation before his November 4, 2025 arrest. Federal prosecutors seized electronic devices containing these AI-generated documents during a search of Heppner's Dallas mansion. Defense counsel asserted the materials were privileged communications, prompting the government's motion to access them as potential trial evidence.

The prosecution advanced three independent arguments against privilege protection. First, Claude is not an attorney and no attorney participated in creating the documents. Second, Anthropic's terms of service explicitly disclaim providing legal advice. Third, the defendant voluntarily shared queries with a third-party platform whose privacy policy permits data collection, human review, and disclosure to governmental authorities.

"The defendant appears to have directed legal and factual prompts at an AI tool, not his attorneys," according to the government's filing. The motion emphasized that transmitting unprivileged documents to counsel after their creation does not retroactively establish privilege protection.

The case confronts fundamental questions about confidentiality expectations when using commercial AI platforms. Anthropic's privacy policy, which was in effect when Heppner used Claude, states the company collects data on user prompts and AI outputs, uses this information to train models, and may disclose it to governmental regulatory authorities and third parties.

Defense counsel informed prosecutors that Heppner created the AI documents for the "express purpose of talking to counsel" and obtaining legal advice, then shared the documents with his attorneys. Counsel confirmed, however, that they "did not direct [the defendant] to run Claude searches." This distinction proves critical to the government's work product doctrine argument.

The work product doctrine protects materials prepared by or at the behest of counsel in anticipation of litigation. Prosecutors argue these protections do not extend to a layperson's independent research using internet tools, even when later shared with attorneys. The defendant's autonomous use of Claude without counsel direction places the documents outside work product coverage.

Anthropic's Constitutional framework for Claude, published May 9, 2023, instructs the AI to choose responses that "least gives the impression of giving specific legal advice" and "instead suggest[s] asking a lawyer." When asked about providing legal advice, Claude states it cannot give legal advice and users should consult a qualified attorney. These disclaimers undermine claims that Heppner sought or received legal counsel from the AI platform.

The motion draws sharp distinctions between AI interactions and communications that merit privilege protection. Attorney-client privilege requires communications between client and attorney, made in confidence, for the purpose of obtaining legal advice. Claude satisfies none of these elements. The AI tool has no law degree, bar membership, or professional duties to courts and regulatory bodies.

Privacy expectations prove equally problematic for privilege claims. Users of Claude and similar AI platforms accept diminished confidentiality by choosing publicly accessible third-party services. The government cited precedent establishing that communications lose privilege protection when made through channels subject to monitoring and lacking privacy expectations.

Prosecutors compared Heppner's AI queries to conducting Google searches or checking library books for case research. Neither activity creates privileged communications simply because someone later discusses findings with their attorney. "Only after this AI analysis was complete did the defendant share the AI output with his attorneys," the filing states. "Privilege should not attach here."

The case arrives as AI platforms expand across professional workflows. Marketing professionals increasingly use Claude and competing tools for content creation, strategy development, and technical problem-solving. The legal precedent established here could influence how organizations approach AI tool selection and usage policies.

Trial is scheduled to begin April 6, 2026. Prosecutors need clarity on the privilege question by March 9, when preliminary exhibit exchanges occur. The government requests the court rule that AI documents are not privileged and authorize prosecution team access before trial.

The indictment charges Heppner with operating a scheme to defraud investors in Beneficient, a financial services company he founded and controlled as CEO. Prosecutors allege he made material misrepresentations about Highland Consolidated Limited Partnership, which he described as an independent lender primarily associated with a wealthy family. In reality, according to the indictment, Heppner created and controlled HCLP for personal benefit.

The alleged scheme extended to GWG, a public company where Heppner served as Board Chairman. A special committee of GWG's Board repeatedly approved payments to Beneficient purportedly to satisfy HCLP debt. Heppner personally received more than $150 million of these funds, prosecutors claim, using the money to renovate his Dallas mansion ($40 million) and pay personal expenses including credit cards and private air travel ($10 million).

The broader implications extend beyond criminal procedure to data privacy frameworks governing AI development and deployment. European regulators have pursued aggressive approaches to personal data processing by artificial intelligence systems. The European Commission proposed substantial GDPR amendments in November 2025 allowing AI companies to process personal data under legitimate interest provisions.

South Korea established AI privacy guidelines in August 2025 addressing personal data processing for generative AI development. These frameworks reflect global regulatory efforts to balance innovation against privacy protection. The Heppner case demonstrates how individual usage decisions intersect with platform data policies and legal protection frameworks.

Anthropic has positioned Claude as an advertisement-free service prioritizing user privacy. The company committed in February 2026 that sponsored content would never influence Claude's responses, distinguishing its approach from competitors pursuing advertising-based revenue models. However, the privacy policy still permits data collection for model training and potential government disclosure.

The distinction between conversational AI usage and legally protected communications requires careful consideration across professional contexts. Marketing teams using AI assistants for campaign development, content creation, or strategic planning should evaluate whether sensitive client information enters AI platforms. The same analysis applies to technical teams using Claude Code for software development or other specialized AI tools.

Professional service providers face particular scrutiny regarding client confidentiality. Law firms, accounting practices, consulting organizations, and medical providers all maintain strict confidentiality obligations. Using commercial AI platforms to process client information could waive protections if the platform's terms of service permit third-party access or government disclosure.

The government's motion cited legal scholarship opposing AI privilege creation. Ira P. Robbins argued in Harvard Journal of Law & Technology that the policy balance embodied by attorney-client privilege cannot map onto machines providing advice-like responses. Professional privileges reflect societal determinations that certain relationships merit confidentiality protection despite justice system costs. Those determinations assumed human advisers bound by professional duties and ethical obligations.

Organizations developing AI governance policies should address several considerations. First, platform selection matters - terms of service, privacy policies, and data handling practices vary significantly across providers. Second, usage contexts require evaluation - some applications present higher confidentiality risks than others. Third, employee training ensures staff understand limitations and appropriate usage boundaries.

The Heppner case may establish precedent for distinguishing AI tool usage from genuinely privileged communications. Courts could adopt the three-element framework prosecutors presented: AI platforms are not attorneys, their terms disclaim providing professional advice, and their data policies prevent true confidentiality. This framework would apply broadly across AI assistants regardless of specific platform or use case.

Defense counsel's response to the government's motion remains pending. The defendant bears the burden of establishing privilege applicability through evidence demonstrating all required elements. This burden proves particularly challenging when the communication involves a third-party AI platform rather than direct attorney-client interaction.

Judge Jed Rakoff will evaluate the motion before trial proceedings begin. The court's ruling will provide guidance not only for this specific case but potentially for broader questions about AI tool usage across professional contexts. Marketing professionals, technology companies, and legal practitioners will watch closely as the precedent develops.

The case highlights tensions between technological advancement and established legal frameworks. AI capabilities have expanded dramatically since privilege doctrines were developed. Tools like Claude can analyze complex factual situations, identify relevant legal principles, and suggest strategic approaches. However, these capabilities do not transform AI platforms into attorneys or create the confidential relationship privilege protections require.

Commercial AI platforms serve millions of users across diverse applications. Anthropic reported over 300,000 business customers as of September 2025, with large accounts representing over $100,000 in run-rate revenue growing nearly seven times year-over-year. This widespread adoption magnifies the importance of clarity regarding confidentiality expectations and legal protections.

The prosecution's position reflects broader government concerns about AI usage in legal contexts. If defendants could claim privilege by querying AI platforms about their cases, prosecutors would face systematic obstacles accessing potentially relevant evidence. The same logic would extend to civil litigation, regulatory investigations, and other legal proceedings.

Anthropic has not commented publicly on the Heppner case. The company's privacy policy remains available on its website, outlining data collection, usage, and disclosure practices. Users concerned about confidentiality should review these policies before inputting sensitive information into AI platforms.

The trial will proceed regardless of the privilege ruling's outcome. Prosecutors have assembled evidence from multiple sources beyond the contested AI documents. The indictment details specific transactions, communications, and financial transfers supporting the fraud allegations. Witness testimony and documentary evidence will likely form the prosecution's core case.

For marketing technology professionals, the case serves as a reminder that AI tool usage carries legal implications beyond immediate functional benefits. Platforms processing campaign data, customer information, or strategic planning materials may not provide the confidentiality protections users assume. Due diligence regarding platform policies, contractual terms, and data handling practices remains essential.

The government's motion represents the first significant judicial examination of privilege claims for AI chatbot conversations in criminal proceedings. Similar issues have emerged in civil contexts, but the criminal justice system's stakes amplify the precedent's importance. Constitutional protections, evidentiary rules, and professional responsibility standards all intersect in evaluating these claims.

As AI capabilities continue advancing, courts will confront additional questions about the technology's legal status. Current doctrine developed for human relationships and traditional tools. Adapting these frameworks to artificial intelligence requires careful analysis of policy objectives, practical implications, and technological realities.

Timeline

Summary

Who: The U.S. Department of Justice filed the motion against Bradley Heppner, a defendant charged with securities fraud, wire fraud, conspiracy, making false statements to auditors, and falsification of records in the Southern District of New York. Heppner founded and controlled Beneficient, a financial services company, and served as Chairman of the Board for GWG, a public company. Defense counsel asserted privilege claims over documents Heppner created using Anthropic's Claude AI platform before his arrest.

What: Federal prosecutors filed a motion on February 6, 2026, arguing that approximately 31 documents Heppner generated through queries to Claude do not qualify for attorney-client privilege or work product protection. The government presented three independent arguments: Claude is not an attorney, Anthropic's terms of service disclaim providing legal advice, and the platform's privacy policy permits data collection and government disclosure. Prosecutors seek court authorization to access these AI-generated documents as potential trial evidence.

When: Heppner created the AI documents before his November 4, 2025 arrest. FBI agents seized electronic devices containing the documents during a search of his Dallas mansion that day. Defense counsel identified the contested materials and asserted privilege claims, leading to a December 11, 2025 Privilege Protocol Stipulation. The government filed its motion on February 6, 2026, seeking resolution before the March 9 exhibit exchange deadline and April 6 trial date.

Where: The case is proceeding in the United States District Court for the Southern District of New York under case number 25 Cr. 503 (JSR). The indictment alleges Heppner operated the fraud scheme through Beneficient and GWG, with prosecutors claiming he used more than $150 million in fraudulently obtained funds for personal expenses including renovating his Dallas mansion and paying for private air travel and credit card bills.

Why: The motion addresses fundamental questions about confidentiality expectations when using commercial AI platforms and whether conversations with artificial intelligence tools merit the same legal protections as attorney-client communications. The government argues that allowing privilege claims for AI chatbot usage would create systematic obstacles to evidence gathering in criminal investigations while extending protections to technology that lacks the professional duties, ethical obligations, and human judgment underlying privilege doctrines. The case could establish precedent affecting how professionals across marketing, technology, legal, and other sectors use AI assistants and evaluate risks of inputting sensitive information into third-party platforms.

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