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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

#291
post #269

Earlier quoted context omitted.

Right, that's the problem. There need to be standards that govern what can ever be released to customers/the public in the first place. When violations of those are discovered, the penalties should be based on time from release, so the longer it was out in the wild, the greater the penalty.

But you can't remove something from the internet once it's there, so once it's released, it's expected that it always will be. It's also impossible to guarantee a 100% secure infrastructure, no matter how good your product team is. In the grey is a term of art: "best efforts." If data is leaking, and it wasn't because hackers bypassed a bunch of safeguards, if it can be shown that you didn't use Best Efforts to secur…

A charitable way of interpreting "best effort" is that it's similar to what I said: we need standards. But the problems with our notion of "best effort" are:

1. The standards aren't clearly defined (i.e., you must specifically do this).

2. They are defined in terms of efforts rather than effects. It is like saying "every car sold must be made of steel" rather than "every car sold must be capable of withstanding an impact against a concrete wall at 60mph with X amount of deformation, etc." We want the rules to determine what level of threat is protected against, not just what motions the company went through. In the case in the article, it wasn't because hackers bypassed a bunch of safeguards; the company didn't protect against even basic threats.

3. It's not enough to have "liability". That puts the onus on individuals to sue the company for their specific damages. We need criminal penalties that are designed to punish companies (and the individuals who direct them) for the harm they do to society by the overall process of rushing ahead selling things instead of slowing down and being careful. We need large-scale enforcement so that companies actually stop doing these things because the cost of doing them becomes too enormous.

4. Our laws do not adequately take account of the differential power of those who cut corners, and the differential gains reaped. We frequently find small operators on the wrong end of painful lawsuits and onerous criminal penalties, while the biggest companies and wealthiest individuals use their position to avoid consequences. Laws need to explicitly take this into account, lowering the standard of proof for penalties against larger, wealthier, and more powerful companies and individuals, and also making those penalties exponentially higher.

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

#292
post #156

Earlier quoted context omitted.

While there were numerous problems with the big corporate structures I worked in decades ago where everything was done by silos of specialists, there were huge advantages. No matter where there was a security, performance, network, hardware, etc. issue, the internal support infrastructure had the specialist’s pagers and for a problem like this, the people fixing it would have been on a conference call until it was fi…

Interesting. Wouldn't the performance department have their fingers in all the pies anyway, too, or how was that handled?

Their job was specifically managing server resource allocation— as an IT role and not a dev role— in a completely standardized environment. Most applications were given a standard allotment of resources, and they only got involved if something was running out of ram, disk access was too slow, or something just seemed to be taking a lot longer than usual. If it seemed to be a network problem, or just a program crash, for example, they were never involved unless troubleshooting indicated it involved them. More often than not, I’d get a phone call telling me the system I was working on seemed to be heavy on the disk access or something, and they had already allotted it more to keep it stable, but I should check to make sure we weren’t doing something stupid.

Now that I think of it, I’ll bet a lot of companies have a system similar to this for their infrastructure… they just outsource it to AWS, Azure, Google, etc. and comparatively fly by the seat of their pants on the dev side. You could only scale that system down so much, I imagine.

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

#293
post #8

Earlier quoted context omitted.

It's a little hilarious. First, as an organization, do all this cybersecurity theatre, and then create an MCP/LLM wormhole that bypasses it all. All because non-technical folks wave their hands about AI and not understanding the most fundamental reality about LLM software being fundamentally so different than all the software before it that it becomes an unavoidable black hole. I'm also a little pleased I used two sp…

Maybe this is the key takeaway of GenAI: that some access to data, even partially hallucinated data, is better than the hoops that the security theatre puts in place that prevents average Joe doing their job. This might just be a golden age for getting access to the data you need for getting the job done. Next security will catch up and there'll be a good balance between access and control. Then, as always security g…

This is not at all what I am saying.

"GenAI" is nothing new. "AI" is just software. It's not intelligent, or alive, or sentient, or aware. People can scifi sentimentalize it if they want.

It might simulate parts of things, hopefully more reliably.

It's however a different category of software which requires management that doesn't exist yet how it should.

Cybersecurity security theatre for me is using a web browser to secure and administer what was previously already done and creating new security holes from a web interface.

Then, bypassing it to allow unmanaged MCP access to internal data moats creating it's own universe of security vulnerabilities, full stop. In a secured and contained environment, using an MCP to access data to unlock insight is one thing.

It doesn't mean dont' use MCPs. It means the AI won't figure out what the user doesn't know about security around securing MCPs which is a far more massive vulnerability because users of AI have delegated their thinking to a statistics formula ("GenAI"), because it is so impressive on the surface, but no one is checking the work to make sure it stays that way. Managing quality however, is improving.

My comment is calling out effectively letting external paths have unadulterated access to your private and corporate data.

Data is the new moat. Not UI/UX/Software.

A wormhole that exposes your data makes it available for someone to put it into their data moat far too commonly, and also for it to be mis-interpretted.

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

#294
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.

Being a sellout is weak and sad.

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

#295
Man. Hopefully their remediation steps included a full audit of their Box's account.

One could only imagine that if OP wasn't the first to discover it, people could've generated tons of shared links for all kinds of folders, for instance, which would remain active even if they invalidated the API token.

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

#296

Earlier quoted context omitted.

You may want to read about agentic AI, you can for instance call an LLM multiple times with different security consideration everytime.

There's about a dozen workarounds around context limits, agents being one of them, MCP servers being another one, AGENTS.md being the third one, but none of them actually solve the issue of a context window being so small that it's useless for anything even remotely complex. Let's imagine a codebase that can fit onto a revolutionary piece of technology known as a floppy drive. As we all know, a floppy drive can store…

You can have an agent that focuses on studying the interactions. What you're saying is that an AI cannot find every security issue but neither do humans otherwise we wouldn't have security breaches in the first place. You are describing a relatively basic agentic setup mostly using your AI-assisted text editor but a commercial security bot is a much more complex beast hopefully. You replace context by memory and synthesis for instance, the same way our brain works.

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

#297

Earlier quoted context omitted.

There's about a dozen workarounds around context limits, agents being one of them, MCP servers being another one, AGENTS.md being the third one, but none of them actually solve the issue of a context window being so small that it's useless for anything even remotely complex. Let's imagine a codebase that can fit onto a revolutionary piece of technology known as a floppy drive. As we all know, a floppy drive can store…

In one instance it could not even describe why a test is bad unit test (asserting true is equal to true), which doesn’t even require context or multi file reasoning. Its almost as if it has additional problems beyond the context limits :)

In an agentic setup you are still dependent on having relatively smart models that's true.

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

#298

Earlier quoted context omitted.

To add onto this, it is a characteristic of their design to statistically pick things that would be bad choices, because humans do too. It’s not more reliable than just taking a random person off the street of SF and giving them instructions on what to copy paste without any context. They might also change unrelated things or get sidetracked when they encounter friction. My point is that when you try to compensate by…

> To add onto this, it is a characteristic of their design to statistically pick things that would be bad choices, because humans do too. Spot on. If we look at, historically, "AI" (pre-LLM) the data sets were much more curated, cleaned and labeled. Look at CV, for example. Computer Vision is a prime example of how AI can easily go off the rails with respect to 1) garbage input data 2) biased input data. LLMs have th…

Talking about the debt of a system prompt feels really weird. A system prompt tied to an LLM is the equivalent of crafting a new model in the pre-LLM era. You measure their success using various quality metrics. And you improve the system prompt progressively to raise these metrics. So it feels like bandaid but that's actually how it's supposed to work and totally equivalent to "fixing" a machine learning model by improving the dataset.

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

#299
post #8
post #4

[flagged]

It's a little hilarious. First, as an organization, do all this cybersecurity theatre, and then create an MCP/LLM wormhole that bypasses it all. All because non-technical folks wave their hands about AI and not understanding the most fundamental reality about LLM software being fundamentally so different than all the software before it that it becomes an unavoidable black hole. I'm also a little pleased I used two sp…

> I'm also a little pleased I used two space analogies, something I can't expect LLMs to do because they have to go large with their language or go home.

Speaking of LLMs, did you notice the comment you were responding to was written by an account posting repetitive LLM-generated comments? :)

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

#300
post #152
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.

It looks like SOC 2 (and the other SOCs) where developed by accountants? I wouldn't expect them to find any computer problems either to be honest.

There are only 3 books of SOC: SOC I, SOC II Part 1, SOC II Part II.
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