Farewell, My Privilege

Imagine this: You are representing the target in a high stakes merger, and a shareholder is seeking an injunction against proceeding with the transaction on the grounds, among others, of breach of Revlon duties and lack of a disinterested board majority. Plaintiff’s depositions have been rolling up the chain and time has come for examining the board members.

Although it’s been something of a slog, and billable hours have been eating into sleep forever, you’re not stressing over much. Your witness is well prepared and a veteran of past depositions.

Opposing counsel adopts an “aw, shucks” Columbo style. He opens with the usual disarming pleasantries.

Q: Wow! Is that a new iPhone?

A: Uh, why yes it is.

Q: Those are so handy. Never miss a message, I bet. Have it with you most of the time?

A: Well, sure

Q: Moving on …

At the break, your client asks you “what was that with all the iPhone business?” And you begin to reply, “oh, nothing,” and then suddenly excuse yourself to go throw up in the corner. Suddenly, you are back in the room where the attorney-client communication privilege was waived.

Why was this?

We’ve all heard by now the sad tale of a litigant who had consulted a chatbot and discovered that his interaction was not a privileged attorney-client communication. But that’s a hearse of a different color.

Hello, Siri?

As of Apple’s iOS 27.0.1 update, AI in the Apple ecosystem has become a selling point.

Siri AI, a profoundly more capable and personal assistant powered by the next generation of Apple Intelligence, is here

— Apple September 14, 2026 announcement

Today, I was missing my wallet and mutter to myself

I’m in big trouble here

— Personal communication from the author to himself

When what should appear without so much as a Hey, Siri!

I’m sorry to hear that. Can I help?

— Siri

Yup, Siri has been eavesdropping on me.

Granted, it was with my constructive consent. Like any normal human being, I do not read the fine print on an EULA (end-user license agreement). I now have.

Apple says many nice things about how highly it respects personal privacy. But take a look yourself. There’s no express duty to hold attorney-client communications in confidence for the purposes of facilitating communications. Unlike e-mail providers, who are a necessary intermediary in the modern chain of client advice, Siri is not a necessary party to the matters disclosed during the course of eavesdropping.

Uh, reference is made to

Rule (1.6(c) A lawyer shall make reasonable efforts to prevent the inadvertent or unauthorized disclosure of, or unauthorized access to, information relating to the representation of a client.

— The ABA Model Rules of Professional Conduct

and

A lawyer sending or receiving substantive communications with a client via e-mail or other electronic means ordinarily must warn the client about the risk of sending or receiving electronic communications using a computer or other device, or e-mail account, where there is a significant risk that a third party may gain access. In the context of representing an employee, this obligation arises, at the very least, when the lawyer knows or reasonably should know that the client is likely to send or receive substantive clientlawyer communications via e-mail or other electronic means, using a business device or system under circumstances where there is a significant risk that the communications will be read by the employer or another third party

— Formal Opinion 11-459

and to the embarrassing lack of protection:

E-mail providers and telecom carriers fall squarely under the statutory protections of the Electronic Communications Privacy Act (ECPA, 18 U.S.C. § 2517(4)), at least as far as criminal investigations go, and state counterparts (e.g., Cal. Evid. Code § 917(b)), mabye,, which explicitly state that a privileged communication does not lose its privileged character solely because it is transmitted by electronic means.¹

Presumptions? Maybe, but is that enough?

Not for MY risk appetite

Paranoia strikes deep
Into your life it will creep

— Steven Stills, For What It’s Worth

By my lights, part of a war room set up is a SCIF (“sensitive compartmentalized information facility”), don’t assume that their corporate security system has this covered by sweeps for bugging devices in the boardroom. (You’ve asked, right?) Ask your client for in-person conferences to turn off their phones, and turn yours off, as well, and counsel your client about the uncertain risks posed by this AI development.²

THIS is what I do

I pay attention to AI implications, as well as stress-testing the models that enable large language models and other systems to pose the danger in the first place. I do more than try to break frontier models, I think about how they might end up breaking us. richardcareaga@protonmail.com