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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

#261
post #246

Earlier quoted context omitted.

This will age badly

That’s why we make concrete measurable predictions.

Agreed, but "vibe coding will be better at security" is not one of them. Better by which metric, against which threat model, with which stakes? What security even means for greenfield projects is inherently different than for hardened systems. Vibe coding is sufficient for security today because it's not used for anything that matters.

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

#262

Earlier quoted context omitted.

Prediction: it won't. You can't fit every security consideration into the context window.

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

And that buys you what, exactly? Your point is 100% correct and why LLMs are no where near able to manage / build complete simple systems and surely not complex ones.

Why? Context. LLMs, today, go off the rails fairly easily. As I've mentioned in prior comments I've been working a lot with different models and agentic coding systems. When a code base starts to approach 5k lines (building the entire codebase with an agent) things start to get very rough. First of all, the agent cannot wrap it's context (it has no brain) around the code in a complete way. Even when everything is very well documented as part of the build and outlined so the LLM has indicators of where to pull in code - it almost always cannot keep schemas, requirements, or patterns in line. I've had instances where APIs that were being developed were to follow a specific schema, should require specific tests and should abide by specific constraints for integration. Almost always, in that relatively small codebase, the agentic system gets something wrong - but because of sycophancy - it gleefully informs me all the work is done and everything is A-OK! The kicker here is that when you show it why / where it's wrong you're continuously in a loop of burning tokens trying to put that train back on the track. LLMs can't be efficient with new(ish) code bases because they're always having to go lookup new documentation and burning through more context beyond what it's targeting to build / update / refactor / etc.

So, sure. You can "call an LLM multiple times". But this is hugely missing the point with how these systems work. Because when you actually start to use them you'll find these issues almost immediately.

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

#264

Earlier quoted context omitted.

Prediction: it won't. You can't fit every security consideration into the context window.

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 kilobytes. So, to process the whole codebase that can fit onto a floppy drive, you need 5 agents plus the sixth "parent process" that those 5 agents will report to.

Those five agents can report "no security issues found" in their own little chunk of the codebase to the parent process, and that parent process will still be none the wiser about how those different chunks interact with each other.

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

#265
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.

Something I've found useful is just reaching out to past employees. Usually folks that don't work there anymore will be more transparent. Only challenge is getting someone to respond to you, but you'd be surprised how many folks will talk if you don't come off like you're trying to sell them something or a bot.

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

#266
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. (…

Once this type of issue gets publicized, does that in anyway affect the certification?

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

#267
post #223

If they have a billion dollar valuation, this fairly basic (and irresponsible) vulnerability could have cost them a billion dollars. If someone with malice had been in your shoes, in that industry, this probably wouldn't have been recoverable. Imagine a firm's entire client communications and discovery posted online. They should have given you some money.

Who says they didn't give him money?

I reckon he would've mentioned it if he got a bounty, 100% deserves the bag

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

#268

Earlier quoted context omitted.

Prediction: it won't. You can't fit every security consideration into the context window.

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

You may want to try using it, anecdotes often differ from theories, especially when they are being sold to you for profit. It takes maybe a few days to see a pattern of ignoring simple instructions even when context is clean. Or one prompt fixes one issue and causes new issues, rinse and repeat. It requires human guidance in practice.

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

#269
post #174

Earlier quoted context omitted.

It does. Most privacy laws are based on time-from-discovery. If they immediately sprung into action at the moment they were informed and remediated the issue, they're in compliance.

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 secure said data, there is liability.

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

#270

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…

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 :)

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