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New case law just dropped[^1]: a guy was charged with a $300M securities fraud. Before his arrest he used Claude (the consumer product) to research his own legal situation. He then handed the outputs to his defense counsel and claimed attorney-client privilege. The prosecutor said "no, that's not how this works, that's not how any of this works", and the judge agreed[^2]. That means that as of this decision, precedent says that if you go to chatgpt dot com and say "hey chatgpt, give me some" legal advice, that's not covered under attorney-client privilege.
On the one hand, duh. On the other hand, it really feels like there should be a way to use LLMs as part of the process of scalably getting legal advice from an actual attorney while retaining attorney-client privilege.
I expect there's an enormous market for "chat with an AI in a way that preserves attorney-client privilege", and as far as I can tell it doesn't exist.
It was also interesting to read the specific reasoning given for why attorney-client privilege was not in play:
I notice that none of these reasons are "conversations with AI are never covered by attorney-client privilege." They're all mechanical reasons why this particular way of using an AI doesn't qualify. Specifically:
The prosecutor also argues that feeding what your attorney told you into your personal Claude instance waives attorney-client privilege on those communications too. If a court were to agree with that theory, it would mean that asking your LLM of choice "explain to me what my lawyer is saying" is not protected by default under attorney-client privilege. That would be a really scary precedent.[^4]
Anyway, I expect there's a significant market for "ask legal questions to an LLM in a way that is covered by attorney-client privilege", so the obvious questions I had at this point were:
For question 1, I think the answer is "no" - a cursory google search[^5] mostly shows SEO spam from
So then the question is "why doesn't this exist" - it seems like it should be buildable. Engineering-wise it is pretty trivial. It's not quite "vibe code it in a weekend" level, but it's not much beyond that either.
After some back-and-forth with Claude, I am under the impression that the binding constraints are
None of these seem insurmountable to me. I'm picturing a workflow like
Anyone with a legal background want to chime in about whether this is a thing which could exist? (cc @faceh in particular, my mental model of you has both interest and expertise in this topic)
[^1]: [United States v. Heppner, No. 25 Cr. 503 (JSR) (S.D.N.Y. Feb. 6, 2026)] (https://storage.courtlistener.com/recap/gov.uscourts.nysd.652138/gov.uscourts.nysd.652138.22.0.pdf). The motion is well-written and worth reading in full. [^2]: Ruled from the bench on Feb 10, 2026: "I'm not seeing remotely any basis for any claim of attorney-client privilege." No written opinion yet.
[^3]: This argument feels flimsy, since attorneys send privileged communications through Gmail every day, and Google can and regularly does access email content server-side for reasons other than directly complying with a subpoena (e.g. for spam detection). It could be that the bit in Anthropic's TOS which says that they may train on or voluntarily disclose your chat contents to government authorities is load-bearing, which might mean that Claude could only be used for this product under the commercial terms, which don't allow training on or voluntary disclosure of customer data. I'm not sure how much weight this particular leg even carried, since Rakoff's bench ruling seems to have leaned harder on "Claude isn't your attorney."
[^4]: A cursory search didn't tell me whether the judge specifically endorsed this theory in the bench ruling. So I don't know if it is a very scary precedent, or just would be a really scary precedent.
[^5]: This may be a skill issue - I am not confident that my search would have uncovered anything even if it existed, because every search term I tried was drowned in SEO spam.
First, I am amazed by the selective stupidity of people. A teenager getting sued by the RIAA (do they still exist?) for downloading a copyrighted mp3-file going to the big LLMs for advice is something I can see. I have no idea how to commit a 300M$ securities fraud in the first place, but if I did I would probably find a spare couple of thousands to discuss my troubles with a lawyer in person.
Also, this is a priesthood ruling that entities who are not ordained priests are not allowed to function as priests. Zero surprise there.
Your workaround would rely on straw lawyers who just start the chat and leave answering the questions to the LLM. The problem with that approach is that it makes the lawyer liable for all the answers the LLM gives you. After all, if you are in a privileged discussion of your legal woes with your lawyer, and a third party opines that if you just confess to everything, you will not be punished, you would reasonably expect your lawyer to refute that claim, and might sue them if they did not.
The same incentives which makes court not recognize LLM communication as privileged even if it covers topics traditionally covered by lawyers would also make them go after any lawyers who start a LLM session and then do not verify the responses.
I think that this is a case where a technical solution is much more apt to solve the problem than a legal one -- just as it is much easier to encrypt your communication than to prevent the NSA from snooping on it.
In most criminal cases, the FBI has no backdoor to the devices of the suspect (and if the NSA does they would not be willing for that fact to become common knowledge just to convict some fraudster). Also, it seems unlikely that they will have hit random IT service providers with an order to record all communication of a suspect. (NSLs do not cover content, but I guess a judge could likewise force a party to record and gag them about that fact.)
Much more likely is that you and the LLM provider will be hit with a subpoena for recorded information. Thus it is sufficient to ensure that there is no record of your conversation. So you want a LLM provider which does not keep records without a court order, which is probably something you can get at enterprise level. And then you simply buy a thumb drive, install Ubuntu (or whatever) on it, boot it, have your little discussion, turn off your PC and microwave the drive. (Sending a transcript to your meatbag lawyer is riskier but not tremendously so, my understanding is that the courts generally do not snoop on lawyer communication in case there is something not covered by client-attorney-privilege. Just do not use your normal mail account!)
Of course, the seriously paranoid will want to run an open-weight LLM locally instead, or at least use a Chinese one whose operators are much less likely to cooperate with US authorities.
It's pretty obvious from the context here that this guy wasn't just trying to get background information of looking up the definition of "included offense"; if that were the case it's unlikely his attorney would even contest handing over the documents. He was probably laying out what he did in detail and trying to see if the LLM's advice corresponded to what his attorney was telling him, or doing something else that required him to disclose incriminating information.
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