There is a particular kind of client that practices in Naples, Marco Island, and Bonita Springs serve every day: highly intelligent, exceptionally resourceful, and thoroughly accustomed to solving problems with the best tools available. They built their businesses by being early adopters. They manage their own research. And in 2026, they are using AI — often before they ever pick up the phone to call their attorney.
A federal judge just ruled that when they do that, the documents they create may not be privileged.
On February 10, 2026, Judge Jed Rakoff of the Southern District of New York ruled in United States v. Heppner that 31 documents created by a defendant using Claude — Anthropic's AI assistant — were not protected by attorney-client privilege and not shielded by the work product doctrine. The government got them. All of them.
For Southwest Florida attorneys advising high-net-worth clients in estate planning, real estate transactions, trust litigation, and business disputes, this is not an abstract academic development. It is a live risk that walked into your office with your last new client.
The Ruling, Plain and Simple
Bradley Heppner, facing federal charges, used Claude to analyze documents before sharing them with his legal team. He argued the resulting AI outputs were covered by attorney-client privilege because he eventually used them in his legal representation.
Judge Rakoff disagreed. His reasoning broke down into three clear principles that apply equally in the Middle District of Florida:
Claude is not a lawyer.
Privilege attaches to communications between a client and their attorney — not between a client and a software platform. No matter what a client tells Claude, how sensitive the information is, or what they ultimately do with the output, no attorney-client relationship forms with an AI. There is no fiduciary duty, no ethical obligation, and no legal protection.
Consumer AI platforms aren't confidential.
The court found that Anthropic's privacy policy — which notified users it collects inputs and outputs to improve its tools and may share data with third parties — destroyed any reasonable expectation of privacy. In Florida, as in New York, confidentiality is a foundational requirement for privilege. If the company processing your data can use and share it, the communication isn't confidential in any legally meaningful sense.
The attorney didn't direct it.
Heppner used the AI on his own. His lawyers didn't tell him to do it, didn't supervise what he asked, and weren't involved in shaping the analysis. Documents created without attorney direction don't reflect attorney strategy or mental processes — a baseline requirement for work product protection.
The Language That Should Be on Every Naples Attorney's Radar
Judge Rakoff's ruling isn't just a prohibition — it contains an affirmative roadmap. He explicitly noted:
"If counsel had directed Heppner to use the AI tool, 'Claude might arguably be said to have functioned in a manner akin to a highly trained professional who may act as a lawyer's agent within the protection of the attorney-client privilege.'"
Attorney-directed. Lawyer's agent. Within the privilege.
That sentence is the legal framework for responsible AI use in your practice. For Southwest Florida attorneys who want to stay competitive with the large Miami firms clients retain for their most complex matters, it defines exactly what separates legitimate AI-powered legal work from a privilege trap.
Why This Hits Southwest Florida Especially Hard
The legal market in Collier County and Lee County is dominated by the kinds of matters where document-intensive AI use is most tempting — and where the privilege stakes are highest.
Estate Planning and Trust Litigation
Naples is home to some of the wealthiest retirees in the country. Many came from business careers where they used technology as a competitive advantage. It is completely natural for a client facing a contested trust to feed documents into Claude and ask it to "find the weak spots in this trust" before calling an attorney. Under Heppner, those AI sessions are potentially discoverable. In a trust contest in Collier County probate court, that could be devastating.
Real Estate Disputes
Southwest Florida's real estate market generates constant litigation — contract disputes, developer fraud claims, partition actions, construction defects. Sophisticated clients with large real estate portfolios often analyze their own documents first. If they used AI to do that analysis, the other side may now be entitled to see it.
Business Succession and Partnership Disputes
Family business disputes frequently involve one party who used AI to model their position before retaining counsel. Those documents — the prompts, the outputs, the analysis — may be fair game under this ruling.
Seasonal Residents Facing Multi-State Issues
Many Naples clients split time between Florida and northern states. They have legal matters in multiple jurisdictions. They use AI habitually. Your role as Florida counsel includes advising them on the privilege implications of what they've been doing in their off-hours with ChatGPT.
The Florida Bar's Emerging Position
The Florida Bar has been among the more progressive state bars on attorney AI use. The Bar's Professional Ethics Committee has issued preliminary guidance that attorneys have a duty of technological competence under Rule 4-1.1, which includes understanding the privacy and privilege implications of AI tools used in practice.
The Heppner ruling adds significant urgency to that guidance. Florida attorneys should anticipate:
- Motions to compel AI-generated documents in discovery disputes in Florida's state and federal courts
- Ethics opinions specifically addressing whether attorneys must advise clients about AI privilege risks as part of competent representation
- Malpractice exposure for attorneys whose clients suffer harm because they weren't warned that their consumer AI use could become discoverable
The Collier County Bar Association has not yet issued formal guidance on this specific ruling, but the implications for local practice are direct. Naples attorneys who stay ahead of this issue — by updating client engagement letters, adding AI advisory language to intake, and using properly structured AI tools in their own practice — will be better positioned than those who wait for formal bar guidance.
What Responsible AI Use Looks Like in a Naples Practice
The Heppner ruling does not say attorneys cannot use AI. It says AI must be used in a way that preserves the structures privilege law depends on. For a Naples solo practitioner or small firm, that means three things:
Your own AI tools need to be attorney-directed by design.
This means using platforms specifically built for legal workflows, where the attorney controls the analysis, where data is isolated to your firm, and where no client information is used to train third-party AI models. Consumer tools — Claude.ai, ChatGPT, Gemini — don't meet this standard because their privacy policies explicitly permit data use that destroys the confidentiality element of privilege.
Educate your clients explicitly.
Add language to your engagement letters noting that clients should not use consumer AI tools to analyze case-related documents without consulting you first. Your clients in Naples are sophisticated enough to understand the issue — they just need to be told. This communication also protects you if a client uses AI without your knowledge.
Your AI-assisted work product needs a defensible structure.
When you use AI in your practice — to analyze discovery documents, generate privilege logs, extract timelines — those outputs should be traceable to your direction, generated within a platform with verifiable confidentiality protections, and documented so you can demonstrate attorney supervision if the issue ever arises in litigation.
How CaseIntel Was Built for This Moment
CaseIntel is an AI-powered legal discovery platform designed specifically for solo practitioners and small firms. Every aspect of how it works is structured around the standard Judge Rakoff described as privilege-preserving.
All AI Analysis Runs at Attorney Direction
There is no client-facing consumer interface. The attorney uploads documents, directs the analysis, and controls how outputs are used. The AI functions exactly as Judge Rakoff described — as an agent of the attorney within the privilege framework.
Data Never Leaves Attorney Control
CaseIntel processes everything through AWS Bedrock on Anthropic Claude models, entirely within US-based AWS infrastructure. Client data is never used to train AI models. It is never shared with third parties. Each firm's data is isolated in a verified multi-tenant architecture.
Privilege Detection Is Automated and Cited
CaseIntel's privilege detection layer scans every document uploaded and flags attorney-client communications, work product, and other protected categories before analysis proceeds. Every flag is cited to the specific language that triggered it, giving the attorney a documented, defensible privilege determination process.
Exports Match Florida Litigation Requirements
CaseIntel generates court-ready privilege logs in standard Florida format, discovery bundles with Bates numbering, and structured exports compatible with Florida state and federal court practice. For Naples attorneys serving clients in the Twentieth Judicial Circuit or the Middle District of Florida, these outputs integrate directly into your existing workflow.
A Practical Checklist for Naples Attorneys
Before your next client meeting, review these five points:
Does your engagement letter address client AI use?
Add a paragraph advising clients not to use consumer AI tools to analyze documents related to their matter without your guidance.
Do the AI tools in your practice have documented confidentiality protections?
If you're using a consumer AI tool to draft documents or analyze case files, check the privacy policy. If it permits training use or third-party sharing, it may not meet the Heppner standard.
Can you document attorney direction for your AI-assisted work?
Keep records showing that AI was used at your direction, as part of your legal analysis — not as an autonomous client-side tool.
Have you reviewed existing client files for AI exposure?
If you have active clients who may have used AI before retaining you, that conversation is worth having now rather than during discovery.
Are your privilege logs generated with documented attorney review?
Under Heppner, the key issue is attorney oversight. If your AI generates a privilege log and you review and certify it, you're likely in a defensible position. Without documented review, you may have a problem.
The Bottom Line for Southwest Florida
The Heppner ruling is a gift to attorneys who understand it. It draws a clear line between risky consumer AI use and properly structured attorney-directed AI — and tells courts, clients, and opposing counsel exactly what to look for. Naples attorneys who position themselves as advisors on responsible AI use will be ahead of every firm that treats this as someone else's problem.
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Start Free TrialFrequently Asked Questions
Does the Heppner ruling apply in Florida state courts?
The Heppner ruling came from the SDNY, but its reasoning applies to the Middle District of Florida as well. The three-part analysis — no attorney-client relationship with AI, no confidentiality in consumer tools, no attorney direction — is grounded in principles of privilege law that apply across Florida's federal courts and will influence state court proceedings.
What types of Naples clients are most at risk under the Heppner ruling?
High-net-worth clients in estate planning and trust litigation, real estate disputes, business succession matters, and clients who split time between Florida and other states are particularly at risk. These clients are sophisticated enough to use AI habitually and have the most to lose from discoverable AI sessions.
What should I add to my Naples law firm's engagement letter about AI?
Add a paragraph advising clients not to use consumer AI tools (ChatGPT, Claude, Gemini, Perplexity) to analyze documents, communications, or information related to their legal matter without first consulting you. Explain briefly that such use may render those documents discoverable by opposing parties.
How does CaseIntel satisfy the Heppner ruling's privilege-preserving standard?
CaseIntel has no client-facing interface — all analysis is attorney-directed. Data is processed through AWS Bedrock entirely within US infrastructure, never used to train AI models, and never shared with third parties. The platform generates privilege logs in Florida court format with documented attorney supervision.
This article is for informational purposes only and does not constitute legal advice. For guidance specific to your Florida practice, consult The Florida Bar's Ethics Hotline or Collier County Bar Association.
Further Reading
- United States v. Heppner, No. 1:23-cr-00251 (S.D.N.Y. Feb. 10, 2026) (Rakoff, J.)
- The Florida Bar — Technology and the Practice of Law Resources
- Collier County Bar Association