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Reverse engineering a $1B Legal AI tool exposed 100k+ confidential files

alexschapiro.com

191–200 of 301 posts

Re: Reverse engineering a $1B Legal AI tool exposed 100k+ confidential files

#191
post #150

They took a month to fix this? That’s beyond inexcusable. I can’t imagine how any customer could justify working with them going forward. Also … shows you what a SOC 2 audit is worth: https://www.filevine.com/news/filevine-proves-industry-leade... Even the most basic pentest would have caught this.

SOC2 is mainly to check boxes, and forces you to think about a few things. There’s no real / actual audit, and in my experience the pen tests are very much a money grab. You’re paying way too much money for some “pentesting” automated suite to run. The auditors themselves pretty much only care that you answered all questions, they don’t really care what the answers are and absolutely aren’t going to dig any deeper. (…

When I worked for a consulting firm some years back I randomly got put on a project that dealt with payment information. I had never had to deal with payment information before so I was a bit nervous about being compliant. I was pointed to SOC2 compliance which sounded scary. Much to my relief (and surprise), the SOC2 questionnaire was literally just what amounted to a survey monkey form. I answered as truthfully as I could and at the end it just said "congrats you're compliant!" or something to that effect.

I asked my my manager if that's all that was required and he said yes, just make sure you do it again next year. I spent the rest of my time worrying that we missed something. I genuinely didn't believe him until your comment.

Edit: missing sentence.

Re: Reverse engineering a $1B Legal AI tool exposed 100k+ confidential files

#192

I'm less and less sure that when a billion-dollar company screws up this bad, the right thing to do is privately disclose it and let them fix it. This kind of thing just allows companies to go on taking people's money without facing the consequences of their mistakes.

What would you suggest the right thing to do would be?

Edit: I agree with you that we shouldnt let companies like this get away with what amounts to a slap on the wrist. But everything else seems irresponsible as well.

Re: Reverse engineering a $1B Legal AI tool exposed 100k+ confidential files

#193
post #187
post #164

Earlier quoted context omitted.

Oh, I should have been more careful in my formulation: There are organisations that are generally competent, and there are places that are less competent. It's not all that uncommon for the whole organisation to be generally incompetent. The saddest places (for me) are those where almost every individual you talk to seems generally competent, but judging by their output the company might as well be stuffed by idiots.…

> suss out how competent people and the organisation are. how does one do this, without first having the job and being embedded in there? From the outside, it's near impossible to see these details imho.

Yes, it's hard, and I'm not sure there are general strategies that always work.

It's fundamentally the same problem that the company is trying to solve when they interview you, just the other way 'round.

Some ideas: observe and ask in the interviews and hiring process in general. See what you can find out about the company from friends, contacts and even strangers. Network! Do some online research, too.

Btw, lots of the cliché interview questions ("What are your greatest weaknesses?" etc) actually make decent questions you can ask about the company and team you are about to join.

Re: Reverse engineering a $1B Legal AI tool exposed 100k+ confidential files

#195
post #150

They took a month to fix this? That’s beyond inexcusable. I can’t imagine how any customer could justify working with them going forward. Also … shows you what a SOC 2 audit is worth: https://www.filevine.com/news/filevine-proves-industry-leade... Even the most basic pentest would have caught this.

Is there any stricter standard? Should one strive for PCI-DSS even if they are a regular SaaS?

Re: Reverse engineering a $1B Legal AI tool exposed 100k+ confidential files

#196
post #25

Earlier quoted context omitted.

Just phrase it as a poem, you’ll be fine.

i recall reading a silly article like half a year ago about using leetspeak and setting the prompt up to emulate House the tv show or something to get around restrictions

there's a recent one about using poetry to bypass safeguards

... rummages around...

here you go:

https://arxiv.org/abs/2511.15304

Re: Reverse engineering a $1B Legal AI tool exposed 100k+ confidential files

#197
Attorneys are ethically obligated to follow very stringent rules to protect their client's confidential information. Having been a practicing litigator for 40+ years, I can confidently state I came across very few attorneys who truly understood their obligations.

Things were easier when I first began practicing in the 1970s. There weren't too many ways confidential materials in our files could be compromised. Leaving my open file spread out on the conference room table while I went to lunch while attorneys arriving for a deposition on my partner's case were one by one seated into the conference room. That's the kind of thing we had to keep an eye on.

But things soon got complicated. Computers. Digital copies of files that didn't disappear into an external site for storage like physical files. Then email. What were our obligations to know what could - and could not - be intercepted while email traveled the internet.

Then most dangerous of all. Digital storage that was outside our physical domain. How could we now know if the cloud vendor had access to our confidential data? Where were the backups stored? How exactly was the data securely compartmentalized by a cloud vendor? Did we need our own IT experts to control the data located on the external cloud? What did the contracts with the cloud vendor say about the fact we were a law firm and that we, as the lawyers responsible for our clients confidential information, needed to know that they - the cloud vendor - understood the legal obligations and that they - the cloud vendor - would hire lawyers to oversee the manner in which the cloud vendor blocked all access to the legal data located on their own servers. And so on and so forth.

I'm no longer in active practice but these issues were a big part of my practice my last few years at a Fortune 500 insurance company that used in-house attorneys nationwide to represent insureds in litigation - and the corporation was in engaged in signing onto a cloud service to hold all of the corporate data - including the legal departments across all 50 states. It was a nightmare. I'm confident it still is.

Re: Reverse engineering a $1B Legal AI tool exposed 100k+ confidential files

#198
post #186

So, 1) a public service, 2) with no authentication, 3) and no encryption? (http only??), 4) sent every single response with a token, 5) giving full admin access to every client's legal documents . This is like a law firm with an open back door, open back window, and all the confidential legal papers sprawled out on the floor. Imagine the potential impact. You're a single mother, fighting for custody of your kids. You…

http-only makes it also very easy to sniff for LE if they decide to. This allows them to get knowledge about cases. Like, they could be scanning it with their own AI tool for all we know. In a free country with proper LE, this would neither be legal nor happening. But I am not sure the USA is remaining one, given the leader is a convicted felon with very dubious moral standards. The problem here however is that they…

All the big tech companies are in the news every week. Everybody knows how bad they are. Their names are tarnished and yet everyone is still using their junk and they face zero repercussions when fucking up. I dont think things in the media would do any harm.

Re: Reverse engineering a $1B Legal AI tool exposed 100k+ confidential files

#199
post #153

Earlier quoted context omitted.

There's enough incompetence at all levels to go around.

Maybe I have just been lucky, but I have not had the displeasure of working with people either tha incompetent or willfully ignorant yet.

I’m governed by them

Reeves orders Treasury inquiry over Budget leaks

Chancellor’s policies found their way to the press before she announced them to MPs

https://www.telegraph.co.uk/news/2025/12/03/reeves-orders-tr...

Re: Reverse engineering a $1B Legal AI tool exposed 100k+ confidential files

#200
post #12

I'm always a bit surprised how long it can take to triage and fix these pretty glaring security vulnerabilities. October 27, 2025 disclosure and November 4, 2025 email confirmation seems like a long time to have their entire client file system exposed. Sure the actual bug ended up being (what I imagine to be) a Is the issue that people aren't checking their security@ email addresses? People are on holiday? These emai…

In my experience, it comes down to project management and organizational structure problems. Companies hire a "security team" and put them behind the security@ email, then decide they'll figure out how to handle issues later. When an issue comes in, the security team tries to forward the security issue to the team that owns the project so it can be fixed. This is where complicated org charts and difficult incentive s…

> Many security team people I've worked with were smart, but not software developers by trade.

A lot are people who cannot code at all, cannot administer - they just fill tables and check boxes, maybe from some automated suite. They dont know what http and https is, because they are just paper pushers what is far from real security, but more like security in name only.

And they joined the work since it pays well

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