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

alexschapiro.com

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

#91
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…

Oh man this is so true. In this sort of org, getting something fixed out-of-band takes a huge political effort (even a critical issue like having your client database exposed to the world).

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

#92
post #89

It's so great that they allowed him to publish a technical blog post. I once discovered a big vulnerability in a listed consumer tech company -- exposing users' private messages and also allowing to impersonate any user. The company didn't allow me to write a public blogpost.

"Allow"? Go on write your blog post. Don't let your dreams be dreams.

Presumably they were paid for finding the bug and inn accepting relinquished their right to blog about it.

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

#93

Earlier quoted context omitted.

Every other headline and conversation having ai is super annoying. But also, its super annoying to sift through people saying "the word critical was used, this is obviously ai!". not to mention it really fucking sucks when you're the person who wrote something and people start chanting "ai slop! ai slop!". like, how am i going to prove is not AI? I can't wait until ai gets good enough that no one can tell the differe…

LLMs will never get good enough that no one can tell the difference, because the technology is fundamentally incapable of it, nor will it ever completely disappear, because the technology has real use cases that can be run at a massive profit. Since LLMs are here to stay, what we actually need is for humans to get better at recognising LLM slop, and stop allowing our communication spaces to be rotted by slop articles…

Do you think the original comment posted by quapster was "slop" equivalent to a copy-paste spam bot?

The only spam I see in this chain is the flagged post by electric_muse.

It's actually kind of ironic you bring up copy-paste spam bots. Because people fucking love to copy-paste "ai slop" on every comment and article that uses any punctuation rarer than a period.

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

#94

It's so great that they allowed him to publish a technical blog post. I once discovered a big vulnerability in a listed consumer tech company -- exposing users' private messages and also allowing to impersonate any user. The company didn't allow me to write a public blogpost.

Why is the control of publication in their hands and not in yours? Shouldn’t you be able to do whatever after disclosing it responsibly?

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

#96

I work for a finance firm and everyone is wondering why we can store reams of client data with SaaS Company X, but not upload a trust document or tax return to AI SaaS Company Y. My argument is we're in the Wild West with AI and this stuff is being built so fast with so many evolving tools that corners are being cut even when they don't realize it. This article demonstrates that, but it does sort of beg the question…

It doesn't sound like your firm does any diligence that would actually prevent you from buying a vendor that has security flaws.

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

#97
post #89

Earlier quoted context omitted.

"Allow"? Go on write your blog post. Don't let your dreams be dreams.

Presumably they were paid for finding the bug and inn accepting relinquished their right to blog about it.

No, you relinquish the right when you agree to their TOS irrespective of if they pay you.

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

#98

Earlier quoted context omitted.

LLMs will never get good enough that no one can tell the difference, because the technology is fundamentally incapable of it, nor will it ever completely disappear, because the technology has real use cases that can be run at a massive profit. Since LLMs are here to stay, what we actually need is for humans to get better at recognising LLM slop, and stop allowing our communication spaces to be rotted by slop articles…

Do you think the original comment posted by quapster was "slop" equivalent to a copy-paste spam bot? The only spam I see in this chain is the flagged post by electric_muse. It's actually kind of ironic you bring up copy-paste spam bots. Because people fucking love to copy-paste "ai slop" on every comment and article that uses any punctuation rarer than a period.

> Do you think the original comment posted by quapster was "slop" equivalent to a copy-paste spam bot?

Yes: the original comment is unequivocally slop that genuinely gives me a headache to read.

It's not just "using any punctuation rarer than a period": it's the overuse and misuse of punctuation that serves as a tell.

Humans don't needlessly use a colon in every single sentence they write: abusing punctuation like this is actually really fucking irritating.

Of course, it goes beyond the punctuation: there is zero substance to the actual output, either.

> What's wild is that nothing here is exotic: subdomain enumeration, unauthenticated API, over-privileged token, minified JS leaking internals.

> Least privilege, token scoping, and proper isolation are friction in the sales process, so they get bolted on later, if at all.

This stupid pattern of LLMs listing off jargon like they're buzzwords does not add to the conversation. Perhaps the usage of jargon lulls people into a false sense of believing that what is being said is deeply meaningful and intelligent. It is not. It is rot for your brain.

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

#99

Earlier quoted context omitted.

And jail time for executives who are responsible for data leaks.

Are you saying executives cannot make mistakes ever (ask because you didn't qualify your statement)?

I'm saying that if executives get praise and bonuses for when good things happen, they should also have negative consequences when bad things happen. Litigate that further how you wish.

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

#100
I mean... in what world would you send a customers private root key to a web browsing client. Like even if the user was authenticated why would they need this? This sort of secret shouldn't even be in an environment variable or database but stored with encryption at rest. There could easily have been a proxy service between client and box if the purpose is to search or download files. It's very bad, even for a prototype... this researcher deserves a bounty!
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