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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.
Seems like this judge might have just invented a multi-billion dollar market in legal LLMs run by your lawyer and covered under attorney-client privilege. Have your lawyer spin up an LLM in a box that’s specifically between you and your lawyer. At least, if my lawyer sends me an email that’s covered so there must be some workaround equivalent.
Yeah, I think the solution here is not "found a new AI company to be Lawyer In A Box" but rather get a lawyer if you think you're going to court, then get them to use AI if either or both of you think this would help. Sounds on the face of it that the guy was trying to be his own lawyer, and that won't wash with any judge.
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Yeah, my instinct is that would work. Instead of querying the LLM directly, the client sends the query to a lawyer who runs the query himself and sends the result back with a disclaimer that the output looks reasonable but he hasn't reviewed in detail -- something that he is happy to do for an extra fee. Just my instinct here, but I think that if (1) the lawyer did not get greedy and fully automate the process; and (2) actually reviewed each LLM response to make sure it wasn't off-the-wall, then you would have a good argument that the privilege applies.
So I guess there will still be some work for lawyers after the AI revolution beyond courtroom work and formal appearances for corporations.
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