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It's not reliable, and presenting it as-such shows a lack of understanding of basic security posture.

Don't take my word for it, watch the news in <6 months and we'll certainly see it get bypassed.

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Maybe that's a hot take, but it's probably still safer than how things are often done in reality when employees want to "get something done" and sign up for random services, download their own software or other variants of shadow IT.
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Completely agree.

This posture is applicable while we ease out of what I'm calling the "golden era" (loose restrictions on access with limited consequence) but one of the reasons I am pedantic and bearish about solutions like this is that they too have a short lifespan that we can already estimate the expiration date of.

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We assume LLMs can always be fooled, so the judge is just one step of the verification process. The deterministic layers, per-tool db roles, read-only-by-default integrations, query timeouts, are the ones an admin can configure. The judge's rules aren't exposed to admins today. I like your idea of letting admins add their own rules or knowledge to the judge, we should add that.
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One of the core issue here is LLMs are probabilistic not deterministic, even with set of rules or context , llms are inherently built to make best guess, so my question is how you are ensuring that LLMs are following rules?
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