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“Want to see it quoted on the front page of the New York Times?” Many Florida community association leaders, members and managers have found to their chagrin that this adage applies to many of their texts and emails, in addition to their verbal comments and written letters.
Now, there is a new breach in the walls of personal privacy. A new embarrassment, if not outright legal danger, has arisen from what used to be good old-fashioned problem solving or sleuthing.
Of course, the seed of this danger is new technology. The explosive growth of “Artificial Intelligence” encourages more use by not just Floridians generally, but also includes community association leaders.
Jumping on the bandwagon of AI, litigants face dangers even before they get to the headline grabbing “hallucinations” which are really basic failures or grievous mistakes.
Court proceedings now abound with a new type of AI related documentation. This is triggered by a user (that means you, the reader) typing a search request on open use or open “LLM” large language model systems, which is now open for discovery by opposing litigation parties.
Yes, this means that the query that you type into an open AI search window to “help” may be sought and used against you in court. Yes, that query that quoted your attorney’s confidential conclusions may be open to the other side’s attorney! This is just as if you told your neighbor of your attorney’s opinions and your neighbor was subpoenaed to testify what you said your attorney said to you.
This is not conjecture, or a chicken little “sky is falling” concern. Recently, a Federal Court ruled that an AI user’s communications are not protected by traditional walls against disclosure, whether the attorney-client privilege or the work product doctrine against discovery. A Federal Court incorporated traditional analyses and concluded that the AI query was not confidential when a user types into a publicly available AI platform in connection with a pending criminal investigation.
The facts in United States v. Heppner, (S.D.N.Y. February 17, 2026) reveal that Heppner was charged with securities fraud in a New York federal court. As part of an investigation the Federal government executed a search warrant at Heppner’s home and seized numerous documents and electronic devices, which included thirty-one documents memorializing communications Heppner had with the AI platform “Claude” which is operated by the private company Anthropic. Heppner’s counsel argued that these documents were privileged because Heppner prepared reports which outlined various defense strategies.
The Federal Court explained that the attorney-client privilege protects from disclosure communications between a client and his or her attorney. The AI documents were not communications between Heppner and his attorney because “Claude” is not an attorney.
“[T]he communications between Heppner and Claude were not privileged at the time they took place,” the court stated. “Moreover, even assuming that Heppner intended to share these communications with his counsel and eventually did so, it is black-letter law that non-privileged communications are not somehow alchemically changed into privileged once upon being shared with counsel.”
Similarly, the so-called work product doctrine exception from discovery did not protect these documents because the reports were not prepared at the instruction of Heppner’s attorney, but rather, Heppner acted on his own in preparing these documents. The court concluded:
Generative artificial intelligence presents a new frontier in the ongoing dialogue between technology and the law. Time will tell whether, as in the case of other technological advances, generative artificial intelligence will fulfill its promise to revolutionize the way we process information. But AI’s novelty does not mean that its use is not subject to longstanding legal principles, such as those governing the attorney-client privilege and the work product doctrine. Because Heppner’s use of Claude fails to satisfy either of these rules, the AI Documents do not merit the protections Heppner has claimed.
This case highlights one of the potential unintended consequences triggered by seemingly innocent, everyday use of AI. When an individual accesses AI on his own initiative, any documents created may end up as discoverable in a future lawsuit. This may include phone records, emails, and reports. Thus, as a warning to association officers, directors and employees, though your AI searches might not be an official record subject to a Condominium Act or Homeowners’ Association Act official records access request, court subpoenas and discovery can be much broader than official records boundaries, especially when focused on individuals, not associations! Take care, especially when there are litigation issues, before you access AI!!