What You Tell AI Can (and Will) Be Used Against You
A New Federal Court Ruling Every Connecticut Resident Should Know About
If you’re like most people, you’ve probably typed a question into an AI chatbot. You know they’re not perfect, but it’s a great way to get advice on any number of topics. And if you’re like most people, you probably didn’t give much thought to the privacy of your interaction. It felt pretty private and really, who’s really going to care about your AI searches after all?
Privacy is what one man thought he had when he used an AI bot to help him plan his own legal defense. Guess what? He didn’t have it at all. A federal judge just ruled that what one man shared with AI while planning his legal defense had no confidentiality protection whatsoever. The government got all of it and is allowed to use it against him
If you live in New Milford or anywhere in Litchfield County and you’ve ever used AI to research a legal problem, this ruling is worth understanding. And it’s a perfect illustration of why a real conversation with a real lawyer — a conversation that is actually protected by law — still matters.
The Case: United States v. Heppner
In United States v. Heppner, No. 25-cr-00503-JSR (S.D.N.Y. Feb. 17, 2026), a man facing federal fraud charges used the consumer version of a popular AI platform to work through his legal situation before his arrest. Heppner used Claude to plan strategy, analyze his exposure, and organize thoughts about his defense.
His lawyers argued those conversations were protected by attorney-client privilege. Judge Jed Rakoff of the U.S. District Court for the Southern District of New York disagreed. In a written opinion, the court ruledthat the 31 AI-generated documents were not shielded by attorney-client privilege or the work product doctrine. The government was allowed to use them.
The reason is simple: when you share information with a public AI platform, you are disclosing it to a third party. Courts have found that users have no “reasonable expectation of confidentiality” in those exchanges. What you type into a chatbot is not a private conversation — it is data. Nothing, not even giving the results to a lawyer afterward, can make the data confidential.
Three Things AI Simply Cannot Do For You
1. Protect What You Share
Attorney-client privilege is a legal shield. When you discuss your situation with a licensed attorney in a confidential setting, that information is protected by law, not by a company’s privacy policy. This confidentiality attaches even before you sign up with a firm, even protecting initial consultations. AI platforms, especially free consumer versions, retain your conversations and can be compelled to produce them. Your attorney cannot.
2. Evaluate What Actually Applies to You
AI knows general legal concepts. It does not know the tendencies of our local judges in Litchfield County, or anywhere else in Connecticut. It does not know how Connecticut juries have handled cases like yours, how local police departments respond to requests, or what negotiating strategies work with local insurance adjusters. An experienced personal injury lawyer or criminal defense attorney in New Milford brings judgment that no algorithm can replicate.
3. Stand Up for You
Legal problems require someone to act: file the right documents, challenge the right decisions, negotiate the right settlement. AI generates text. Your lawyer fights for you.
Not Every Law Firm Works the Same Way
We know that calling a law firm can feel intimidating. You’ve seen the Billboard BrosTM those big faces along the highways who promise maximum settlements, but then route you through a call center, and hand you to a case manager you’ve never met. That is not what we do.
When you call Guendelsberger Law Offices, a real member of our team answers. We handle our own intake — no automated screening, no outsourced staff. From your very first call, you are speaking with someone who works here and knows what matters.
That first call is a free consultation. And unlike any conversation with an AI, it is protected by attorney-client privilege the moment you share your information with us. What you tell us stays with us. Full stop.
We have been serving New Milford and Litchfield County since 1983 — not because we run the most ads, but because our clients trust us, send their families to us, and come back when life gets complicated again.
Get a Real Answer. For Free.
If you or someone you know has been hurt in an accident, is dealing with a criminal charge, needs help with a workers’ compensation claim, or has any other legal question in Connecticut — we are here. Call us at (860) 354-4444. Talk to a real person, and get real answers that are protected by law.
► Schedule your free consultation: www.newmilfordlegal.com
This content is for informational purposes only and does not constitute legal advice. For guidance on your specific situation, contact Guendelsberger Law Offices for a free consultation.
