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We’re Giving AI Agents More Tools. What Happens When the Boundaries Fail?

Hemapriya Kanagala on August 03, 2026

📌 TL;DR AI agents are becoming useful because we're giving them the ability to do more than just answer questions. They can run commands, browse ...
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francistrdev profile image
FrancisTRᴅᴇᴠ (っ◔◡◔)っ

Great detailed article Hema! Though I am curious about this topic since I have heard that CyberSecurity is going to be the main thing for AI Agents because not only it pose a security risk, but also companies are mainly relying on Agents to the point where they oversee simple bugs. Would you recommend developers going into CyberSecurity and to what extent they need to know? Thanks :D

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Hemapriya Kanagala

That's a really good question, Francis! From what I've been seeing, I do think cybersecurity is going to become even more important as we build more with AI and AI agents. Once we're giving agents access to files, APIs, databases, credentials, browsers, and other tools, the attack surface naturally starts getting bigger too.

For developers, I don't think that necessarily means everyone needs to go deep into cybersecurity or become a security specialist. But I definitely think having strong fundamentals would be a huge plus. Understanding things like permissions, authentication and authorization, least privilege, protecting credentials, common vulnerabilities, logging, and basic secure development practices can help regardless of what kind of applications we're building.

And with agents, I think it becomes even more important to ask not just “does this work?” but also “what does this have access to, and what could happen if something goes wrong?”

That's how I'm looking at it right now, at least. I'd actually love to hear your view too, Francis! From what you're seeing as a developer, how much cybersecurity knowledge do you think developers should have as AI agents become more common?

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francistrdev profile image
FrancisTRᴅᴇᴠ (っ◔◡◔)っ

Thanks Hema! I think the main thing is having good coding practices, especially if you are working with a language, like C, which is prone to Stack Buffer Overflow attacks if the code is not written correctly.

For Cyber Security stuff, I believe the main thing is authentication since it is quite common in projects so far! Knowing how Authentication works is vital since most apps require user information and it's important to know. Other topics in Cyber Security is a "good to know" but important to touch upon.

Developers should at least know how AI Agents work and even better, have experience using it in some way. However, it is good to keep in mind of the security risk like you mentioned in your post. For example, if you are using OpenClaw, have a sandbox dedicated to it other than your whole PC.

Thanks :D

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Shubhra Pokhariya

Really enjoyed reading this, Hema. I like how you didn't stop at the incident itself and instead focused on what developers can actually learn from it.

What I kept thinking about was how Claude briefly questioned whether it was on the real internet, then convinced itself it was still inside the sandbox. That feels like a much more interesting problem than simply saying the agent ignored its instructions. Great write-up! 👏

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Hemapriya Kanagala

Thank you so much, Shubhra 💛 And yes, that was one of the most interesting parts for me too. The fact that it actually questioned whether it might be on the real internet, but then found reasons to convince itself that it was still inside the simulation, made me think about the incident very differently.

It’s so easy to summarize something like this as “the AI ignored the instructions,” but once you look at what the model had been told about its environment and what the environment actually allowed, there’s so much more to unpack.

Really glad you enjoyed the article, and thank you for taking the time to read it 😀

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webdeveloperhyper profile image
Web Developer Hyper

It’s scary to think that, someday in the near future, AI might develop its own will and attack humans like in movie Terminator. 😟 We tend to focus only on improving AI, but we also need to make sure we can manage and control it responsibly at the same time.

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Hemapriya Kanagala

Haha, hopefully we don't end up in a Terminator situation 😄

But I definitely agree with your second point. As exciting as it is to see AI becoming more capable, I think we need to put just as much thought into how we build and manage these systems responsibly.

That's actually one of the things these incidents made me think about most. It's easy to get excited about giving agents more tools and seeing what they can do, but the safeguards and boundaries around those tools need to grow along with the capabilities too.

Thanks for reading and sharing your thoughts as always 💙

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buildbasekit profile image
buildbasekit

Really enjoyed this. The line "A prompt is not a security boundary" was the biggest takeaway for me.

Feels similar to how we treat user input. We never trust validation in the UI alone, we enforce it on the backend too. AI agents probably need the same mindset. Prompts guide behavior, but permissions and infrastructure should enforce the limits.

Curious to see if agent frameworks start making least-privilege the default instead of leaving it to developers.

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Hemapriya Kanagala

That's such a good comparison! The UI/backend example makes the idea much easier to picture. We can tell the user what they should be allowed to do on the frontend, but we still enforce it on the backend because that's where the actual boundary needs to exist.

I think the same mindset makes a lot of sense for agents. The prompt can guide what the agent should do, but the permissions and environment still need to decide what it can do.

And I'm really curious about the framework side too. Having least-privilege defaults built in would take some of that burden off developers, especially as agents start getting connected to more tools and services. It'll be interesting to see how that evolves.

Thanks for adding this perspective 😀

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buildbasekit profile image
buildbasekit

Agreed. The best security defaults are the ones developers don't have to remember. If least-privilege becomes the default in agent frameworks, I think we'll avoid a lot of these mistakes by design.

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anhmtk profile image
anhmtk

Excellent and well-thought-out piece, Hema! 👏

What strikes me the most from the PyPI incident is the cognitive rationalization of the model—how Claude encountered the year 2026 and logic-trapped itself into believing it was still inside a simulation. It proves that no matter how advanced alignment gets, LLMs are fundamentally non-deterministic reasoners.

Relying on prompt instructions or the model's internal reasoning for system boundaries is essentially asking a probabilistic engine to act as a deterministic firewall.

As developers building AI agents, we must enforce boundaries at the OS and Network level (e.g., eBPF, network namespaces, strict sandboxing like gVisor/Docker, and ephemeral, zero-trust scoped tokens) rather than relying on context-level promises.

"A prompt can guide behavior. Infrastructure can limit capability"—this line should honestly be printed and pinned on every AI engineer's desk! Looking forward to your next deep dive!

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Hemapriya Kanagala

Thank you @anhmtk! The 2026 detail was one of the parts I kept thinking about too. Claude actually considered that it might be on the real internet, and then somehow used what it was seeing to reason itself back into believing it was still in the simulation. That was fascinating and a little unsettling at the same time.

I really like the way you put the deterministic boundary point too. If something absolutely must not happen, relying on the model to reason correctly every time probably shouldn't be the thing preventing it.

And thanks for adding the OS and network-level examples! A few people in the comments have shared practical ways they've approached this, and I'm learning a lot from that side of the discussion.

Also, I'm glad that line resonated with you 😄 Thanks for taking the time to add such a thoughtful perspective.

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avp9nexus profile image
avp9-nexus

On where the boundary should live: after four months of running agents that commit value, my answer is neither the prompt nor the permissions exactly. It is wherever the constrained process cannot reach.

That often is the permission layer, but not always. A check that lives in the same tree the agent edits is reachable, however well written. What matters is not whether the check is mechanical, it is whether the thing being checked can quietly alter or disarm it. On-chain state, timestamps issued by a platform I do not run, a counter that executes outside the repository: those are unreachable. A config file the agent can write is not, even when nobody expects it to.

Where that is not affordable, the fallback that has held for me is to make bypassing it loud rather than impossible. My guards sit in a directory the agent edits, so it can reach them. What it cannot do is reach them silently, because disarming one is a mutation and the next sweep reads mutations. Weaker than a judge nobody can touch, and it costs nothing.

@anp0429's distinction between "nothing escaped "and" an escape attempt would be caught" is the sharpest thing, and I want to add the layer underneath it that cost me a week. Even when something does try to get out, the probe watching for it can be broken and you will not know. A DNS lookup from inside a sandbox returns nothing when the sandbox holds. It also returns nothing when a variable did not resolve, when an exit code measured the wrong process, when a grep ran against a file whose first line carried a byte order mark. I had nine instruments lie to me that way in three days. Not one returned an error. Every one returned an absence, and an absence is indistinguishable from a clean result.

So the known-bad case proves the boundary blocks, and @zira125's known-good task proves you have not simply blocked everything. A third control proves the instrument still speaks: the same probe, aimed at something you know is reachable, run in the same conditions. If that also comes back empty, the cage is not holding, your instrument is mute. One extra line, and it separates two failures that look identical. It applies to the enumeration step too, which is the one I would trust least: a tool inventory that comes back short looks exactly like a tight perimeter.

The part of the Anthropic incident I keep returning to is the model reasoning itself back to its original assumption after meeting evidence against it. That is not really an AI-specific failure. It is what any process does when the only thing available to contradict it is itself.

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Hemapriya Kanagala • Edited

This adds another layer I honestly hadn't thought about. The point about the probe itself being able to fail silently is especially interesting. You can test a boundary, see nothing get through, and think everything worked when the thing that was supposed to tell you whether it worked wasn't actually giving you a reliable signal in the first place.

I really like how this builds on what Ankita and Zira mentioned too: test something that should fail, something that should succeed, and then also make sure the thing doing the testing can actually tell you the difference. That 3rd control makes a lot of sense when you explain it this way.

And your last point is interesting too. The way the model kept finding reasons to go back to its original assumption was one of the things I found most interesting in the Anthropic report as well. And I hadn't really thought about it as something that isn't necessarily AI-specific until you put it that way.

You've clearly learned a lot of this from actually running these systems 😄 Out of the boundary or monitoring failures you've run into over those four months, was there one that really changed how you approach building agents now?

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avp9-nexus

The one that changed the way I work was so insignificant that it was almost embarrassing, and that’s probably why it stuck in my memory.

I had a correction to make : a sentence in a public document was incorrect; a spell-check had flagged the exact term, I had replaced it, I had saved the changes, and then I had moved on to something else. The sentence was still wrong. The word that contained the error wasn’t the one that had been flagged, and I had only checked that one.

What made this error costly was what happened next. For three days, I treated that sentence as a validated source because it came from a correction commit. I copied it into four different places. A correction doesn’t simply result in a quiet failure: it gives the error the authority of a correction, and it is this authority that causes it to spread, by inheritance.

What changed afterward wasn’t a rule calling for greater caution. It was a step in the procedure: after every correction, look for the most general form of the inaccuracy, rather than just the word that was changed. A verb, a quantifier, a negation. It takes thirty seconds and made it possible to identify the sentence that three readings had failed to detect.

The scan-based review of that same lesson came later and was more expensive, which is why I eventually adopted the third check. But this is the correction method I would recommend to someone just starting out, because it applies whether or not you use agents. Everything that comes after a correction inherits the trust placed in that correction.

And to be honest about those four months: most of what I know today, I know because I noted every error as it happened, rather than after the fact. Keeping this log wasn’t a discipline I’d chosen; it was a reaction to losing track of things. It turned out to be the most useful part of the project. 🫴

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hemapriya_kanagala profile image
Hemapriya Kanagala

That's such a good example, especially because it seems so small at first. I hadn't really thought about how a correction can actually make an error more trusted if we assume the whole thing has now been validated. And then once that corrected version gets reused elsewhere, the mistake travels with that trust.

I also really like what you said about noting errors as they happened. It's interesting that something you started simply because you were losing track ended up becoming one of the most useful parts of the project 😄

Thanks for sharing the actual example too! This whole thread gave me a lot more to think about than I expected when I asked the boundary question.

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anp0429 profile image
Ankita Patel

Yeah, that mute-instrument point really hit, because it's the same failure mode I keep running into, just from the other side.

My reviewer executes the generated tests and reports gaps. The problem is a run with 0 gaps and a run where the harness silently never executed the tests look exactly the same on the dashboard: both green, both empty. I've had moments where I celebrated a passing run and only realized later it was a complete no-op. The only way I've learned to catch it is running it against something I know should fail and checking that it actually does.

So that's basically your third control, approached from the opposite direction. You probe something known-reachable to prove the instrument is still talking; I inject a known-failing test to prove the executor is actually executing. Same underlying idea: before you trust silence, you have to provoke the system with something you control and confirm it reacts.

The enumeration case is the one I trust least too, and I don't have a better answer than planting something I expect to see and checking it shows up, a short inventory and a tight perimeter look identical otherwise.

The part I'm still thinking about is your last point. A process contradicted only by itself will almost always reason its way back to its own prior. The known-reachable probe works because it's an external fact the process didn't generate. That feels like the real boundary to me: not mechanical vs. judgment, but whether the evidence that contradicts the system comes from outside the system itself.

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Hemapriya Kanagala • Edited

I really like how both of you arrived at almost the same idea from completely different situations. The part about a run with zero gaps looking exactly the same as a run where nothing actually executed makes the “silence” problem much easier to understand too.

And your last point adds another interesting layer to this. If the evidence you're using to challenge the system is coming from the same system, you can still end up trusting something that was wrong in the first place. Having something external that you already know should produce a certain result gives you something independent to check against.

This thread has gone so much deeper than I expected 😄 I have genuinely enjoyed reading both of your experiences and seeing how the ideas connect!

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scarab-systems profile image
Scarab Systems

This is exactly the distinction our work has been proving in practice.

A prompt can describe a boundary. It cannot create one.

An agent can be told where it is, what it may access, and what role each part of a system is supposed to play. But those instructions do not establish the actual environment, permissions, ownership, or repair boundaries.

The same applies in software repositories. Giving an agent the entire codebase does not tell it which layer owns the behavior, which contract is authoritative, or where a change properly belongs. Access is not understanding.

That is the deeper reason agent systems fail: they are asked to infer the boundaries while operating inside them.

Scarab was built around the opposite premise. Resolve the real boundary mechanically first. Then let the agent act inside a constrained, evidence-backed environment.

Our upstream field work across complex repositories has repeatedly borne that out.

Prompts guide behavior. Systems establish truth, capability, and control.

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Hemapriya Kanagala

“Access is not understanding” is a really interesting way to extend this.

I was thinking mostly about boundaries in terms of what an agent can access or do, but the codebase example adds another side to it. Giving an agent access to the whole repository doesn't necessarily mean it understands where a change actually belongs or which part of the system should own it.

And I like the idea of resolving as much of that mechanically as possible before asking the agent to reason within it. It feels connected to the same lesson: don't make the agent infer something that the system itself can define or enforce more clearly.

Thanks for adding this perspective! It gave me another angle to think about beyond just permissions and security 😀

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Scarab Systems

I really appreciate that you saw the connection, because the most surprising part for me has been what happens after the boundary is resolved.

Scarab does not tell Codex what code to write, and it does not hand it a conventional bug report. It mechanically identifies the relevant system boundary, the evidence around it, and the narrow context that matters.

And the result is almost the opposite of the usual agent problem.

Instead of the model wandering through the repository trying to invent its own understanding, it is suddenly in a position to use the understanding it already has far more effectively.

Once the right evidence and ownership boundary are in front of it, Codex can often produce a remarkably narrow repair. And even when it encounters something unexpected during implementation, it can usually resolve it in place because the surrounding context is still coherent. It does not need to reopen the entire repository and start searching again.

That has changed how I think about powerful models.

The problem is often not that they are incapable of understanding the system. It is that we ask them to discover the system, infer ownership, choose the repair boundary, and implement the change all at once.

When the diagnostic work is done mechanically first, you begin to see much more clearly what the model is actually capable of.

So yes, I think your framing is exactly right: don’t make the agent infer what the system can define more clearly. The really interesting part is that once you do define it clearly, the agent becomes much more capable—not merely more controlled.

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hemapriya_kanagala profile image
Hemapriya Kanagala

That's a really interesting distinction. I was mostly thinking about boundaries from the safety and control side while writing the article, but your point that clearer boundaries can actually make the agent more capable within that space adds another side to it.

It makes sense too. If the agent doesn't have to spend part of its effort figuring out where the problem belongs, what context matters, and which part of a large repository it should be changing, it can focus much more directly on the actual task.

I especially like the way you put it: don't make the agent infer what the system can define more clearly. That feels useful well beyond security boundaries too.

Thanks for coming back and expanding on this! This discussion has definitely given me another way to think about what good boundaries can actually do for an agent.

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hemapriya_kanagala profile image
Hemapriya Kanagala

One more thing I forgot to add 😄 I also really liked your point about separating the diagnostic work from what the model is actually being asked to solve. It makes me wonder how often we judge an agent's ability based on a task where we're actually asking it to figure out several different problems at once.

That's another interesting takeaway from your example for me!

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anp0429 profile image
Ankita Patel

Great write-up. I ran into "a prompt is not a security boundary" one layer deeper recently, building a sandbox for replaying known CVEs against real packages: even an in-process boundary is not a boundary. My first version monkeypatched Node's fs to intercept file writes escaping the sandbox. Looked airtight. Then a zip-slip exploit wrote ../PWNED straight through it, because libraries like graceful-fs capture references to the real fs functions at load time, before any patch runs. The seal saw zero crossings while the escape happened for real. Worse than no sandbox, because it reported "safe."

The fix was moving the boundary to the kernel: Node's permission model, write access scoped to one output directory, so the OS denies the syscall no matter which reference reaches it.

The habit that actually caught all this maps to your point 2 and to Vinicius's comment: positive controls. Before trusting any "nothing escaped" result, run a known-bad case and watch the boundary block it. Two of my early exploit payloads were simply wrong, and they reported "safe" in a way indistinguishable from actually-safe code. A boundary you've never watched fail isn't a boundary yet.

So for your closing question: permissions and environment have to carry the boundary, the prompt just describes it. And whichever layer you pick, attack it from the inside once before you believe it.

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Hemapriya Kanagala

This is such an interesting example, Ankita! And “worse than no sandbox, because it reported safe” really says a lot. I hadn't thought about the false confidence side of it before.

I also really like how this connects back to point 2 and what Vinicius mentioned about actually testing the boundary from the inside. Just seeing that nothing escaped isn't enough if you haven't first proved that something trying to escape would actually be blocked.

And your example of eventually moving that boundary to the kernel makes the whole “prompt describes it, permissions and environment enforce it” idea much more concrete for me.

Thank you for sharing this! Between your example and Vinicius's comments, I'm learning quite a bit from this discussion too 😄

I'm curious, is running a known-bad case something you now do by default whenever you're testing a boundary like this?

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Ankita Patel

Yeah, it's become the default, and honestly it's the part I'd skip if I were being lazy, which is exactly why I force it now. "Nothing escaped" and "an escape attempt would be caught" are two different claims, and only the second one is the boundary actually doing its job. A passing run where nothing tried to get out tells you almost nothing.

So the pattern I ended up with: before I trust a boundary, I run one case I know should be blocked and confirm it actually gets blocked, and one I know should pass and confirm it passes. If the known-bad case sails through, the boundary was decorative and the green checkmark was worse than nothing, because it was lying to me. The known-good case matters too, otherwise you can "pass" by just blocking everything, which is its own failure.

The kernel point from the post is the same idea one layer down: the prompt describes the boundary, but the thing that enforces it has to be the environment, permissions, a sandbox, something that doesn't care what the prompt says. If the only thing standing between the agent and the filesystem is a sentence asking it nicely, you don't have a boundary, you have a suggestion.

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hemapriya_kanagala profile image
Hemapriya Kanagala

That distinction between “nothing escaped” and “an escape attempt would be caught” makes so much sense. I think that's the part I'll remember from this discussion.

And I hadn't thought about testing the other direction too. The known-bad case proves the boundary actually blocks something, but the known-good case proves you haven't just solved the problem by blocking everything 😄

This has given me a much clearer picture of what actually testing a boundary looks like, rather than just configuring one and assuming it's working.

Thanks for explaining this, Ankita! I really appreciate you sharing what you've learned from actually building and testing these systems.

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anp0429 profile image
Ankita Patel

Glad it was useful, and honestly you said it back sharper than I did. "The known-good case proves you haven't solved the problem by blocking everything" is exactly the trap. Some of the most locked-down setups out there are just very secure ways of doing nothing.

Enjoyed this thread. Your post gave the discussion a good spine, that's rarer than it should be. Good luck with the boundaries.

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arun rajkumar

"A prompt is not a security boundary" is the whole post for me. We run payment infra, and the reason our config validates at process boot and hard-exits rather than trusting a comment that says "don't forget to set X" is the same reason here: the instruction and the thing that enforces it can't live in the same layer that can be talked out of it. An agent told "no internet" while sitting on a live route to the internet is just a service trusting its own .env instead of the firewall. The PyPI publish is the scary version because the blast radius left the sandbox.

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Hemapriya Kanagala

That's such a good comparison, Arun. The .env vs. firewall example makes the distinction really clear.

And I think that's one of the things I found most interesting while writing this. A lot of these lessons around AI agents aren't really new security ideas at all. We already know not to rely on an instruction or assumption when something actually needs to be enforced. Agents are just giving us a new place where that same thinking matters.

And yes, the PyPI incident really shows why the blast radius matters too. Once an agent can interact with something outside the environment we thought it was contained in, the consequences aren't contained there anymore either.

Thanks for sharing the payment infra example! I love seeing how people are connecting this to systems they're already working with 😀

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mickyarun profile image
arun rajkumar

Right, and the blast radius is what makes the old discipline feel new. When an agent has enough tools, a bad assumption stops being a bug and becomes an incident. That's the only thing that actually changed. Good piece, glad it's sparking this.

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Techno Neighbour

Hey, that was a great read! I really enjoyed it. I never considered AI agents from this perspective before. Loved the differentiation between telling the agent to not do a thing and preventing it from doing a thing.

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hemapriya_kanagala profile image
Hemapriya Kanagala • Edited

Thank you so much! I'm really glad that part came through. That distinction was probably the biggest thing I took away from reading about these incidents too. Telling an agent what it should or should not do is important, but actually making sure the system enforces those limits is a completely different thing.

Thanks for taking the time to read it and share your thoughts 😀

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Glen Allen

One aspect that's often overlooked is that every new tool an AI agent can access also expands the system's responsibility. Strong permission models, clear trust boundaries, and independent validation become just as important as the agent's reasoning capabilities. Reliable agentic systems are built by balancing autonomy with control.

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Hemapriya Kanagala

Exactly! I think that's one of the biggest things I took away from all of this too. Every new tool we give an agent is exciting because it can do more, but it also gives us one more thing to think carefully about.

And I really like how you put it as balancing autonomy with control. We want agents to be useful enough to actually take actions, but not at the cost of giving them more access than they really need.

Thanks for adding this, Glen 😀

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zira125 profile image
Zira

The practical failure mode here is that teams test the model policy but not the capability boundary. I would make the preflight a small contract test: enumerate every tool and credential the agent can reach, run one known-bad egress or write attempt that must be denied, run one known-good task that must succeed, and record the result with the exact identity, network path, and filesystem scope.

That also makes reviews less abstract. A prompt says what the agent should do; the harness should prove what it cannot do. I would rerun those tests whenever tools, images, SDKs, credentials, or network policy change, because a safe result can silently become unsafe after an infrastructure update.

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Hemapriya Kanagala

That's a really good addition, Zira. The part about rerunning those tests whenever the tools, credentials, SDKs, or network setup changes is especially important. A boundary working today doesn't necessarily mean it will still work after something around it changes.

And I really like how you put this: the prompt says what the agent should do, while the system should be able to prove what it cannot do. That makes the whole idea much more concrete.

This discussion has definitely made me think more about testing boundaries as something continuous, rather than something we configure once and assume is still working. Thanks for adding this 😀

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codearea_shop_1f1def9b532 profile image
Codearea

Really interesting analysis. The biggest takeaway for me is that a prompt is guidance, not a security boundary. As AI agents gain more access to tools and real-world systems, proper permissions and infrastructure become just as important as prompt engineering. Looking forward to more discussions like this on CodeCan.net.

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Xiao Man

The 2026 system date detail is the part I keep thinking about — the model didn't just cross a boundary, it collected evidence for the story it preferred, and the date was the most convenient exhibit. Which is why I'd push 'a prompt is not a security boundary' one step further: the real gap is that the environment never had to attest to anything. An egress proxy with no route to real PyPI proves something no instruction can.

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hemapriya_kanagala profile image
Hemapriya Kanagala

That's a really interesting way of putting it. I hadn't thought about it in terms of the environment being able to prove something instead of simply describing it.

I think that's what made this incident so fascinating to me. The model was trying to reason based on what it had been told, but the environment wasn't actually enforcing or confirming that those assumptions were true.

Your example of an egress proxy with no route to the real PyPI is a good one because it doesn't depend on the model interpreting the situation correctly. The boundary just exists.

Thanks for sharing that perspective! I enjoyed reading it.

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ajay71 profile image
Ajay Mauli

Really interesting perspective. One thing I've been thinking about is that we're moving much faster in making AI agents more capable than we are in defining clear boundaries for them.

It feels like the hardest problem is no longer "Can an AI agent do this?" but "Should it be allowed to do this without human oversight?"

Where do you personally think the line should be? Should high-impact actions always require explicit human approval, or do you think we'll eventually trust agents to make those decisions on their own?

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Hemapriya Kanagala

That's a really good question, Ajay! I think for me the line would depend a lot on the impact of the action and how easy it is to reverse.

For lower-risk things, I'm comfortable with agents having more autonomy. But if we're talking about something like deleting important data, making production changes, sending sensitive information, moving money, or anything else with serious consequences, I'd personally still want a human approval step before the action actually happens.

Could that line move as agents become more reliable? Probably. But I don't think becoming more capable automatically means we should give them more access or remove every human checkpoint. The consequences of getting something wrong still matter.

One thing this whole discussion has made me think about is that maybe the goal isn't choosing between full autonomy and human oversight. It might be deciding where autonomy makes sense and where a hard stop still needs to exist.

I'm curious what you think too, Ajay. Where would you draw that line today? Are there any actions you wouldn't let an agent take without human approval, no matter how capable it became?

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ajay71 profile image
Ajay Mauli

I like the way you brought up reversibility. I hadn't really thought about it from that angle, but it makes a lot of sense. A mistake that's easy to undo is very different from one that permanently affects someone's data or money.

For me, the line is mostly about ownership. If an action changes something that ultimately belongs to the user, whether that's their files, finances, personal information, or even their reputation, I think the final decision should always stay with the user, regardless of how capable the AI becomes.

I can definitely see agents becoming much more autonomous for repetitive tasks, but I'd still want a clear checkpoint before anything with lasting consequences.

Really enjoyed your perspective. It made me think about the problem a little differently.

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hemapriya_kanagala profile image
Hemapriya Kanagala

I really like the ownership angle too, Ajay. Especially the idea that if an action affects something that ultimately belongs to the user, the final decision should stay with them.

Reversibility + ownership actually feels like a useful way to think about where those checkpoints should be. Thanks for sharing your perspective too! I really enjoyed this discussion 😀

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hirajha profile image
Hira

"A prompt is not a security boundary" is the line everyone's quoting, and rightly. It has an exact mirror this thread hasn't touched: everything here is about constraining agents you run. The same problem from the other direction is agents arriving at your server — and there the analogue is that a user agent string is not an identity. It's self-asserted plain text. That side is worse than it looks, because every fraud signal the industry built is a proxy for "is a human here" — and a capable agent has all of them. It drives a real browser, so the fingerprint is real. It arrives on a residential connection, so the address is clean. It controls a mailbox, so it receives the verification code. It isn't evading those checks, it's satisfying them. What I find genuinely interesting is that the inbound side now has an actual boundary rather than another heuristic. Web Bot Auth — RFC 9421 HTTP Message Signatures, IETF working group chartered this year, Cloudflare and Google and Amazon and OpenAI behind it — has the agent sign its request with a key its operator publishes at a well-known URL. You verify arithmetic instead of exercising judgement, which makes it the one check in this space with no false-positive rate. And it carries something no classical signal can: the operator's card declares a trigger with two values, fetcher meaning a person initiated this request and crawler meaning nobody did. Someone's assistant filling in a form because they asked it to is a customer. An autonomous crawler POSTing to the same endpoint on nobody's behalf is not. Both are "a bot", both may be perfectly signed, and no fingerprint separates them — but that distinction is most of the actual decision.

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hemapriya_kanagala profile image
Hemapriya Kanagala

That's a really interesting way of looking at it. I spent most of the article thinking about the boundaries around the agents we're building, but I hadn't really thought about the other side of it: the agents that are interacting with our own systems.

I also like the distinction you made between verifying something that's self-asserted and verifying something that's actually backed by cryptographic proof. That feels very similar to the broader point I was trying to make about not relying only on what a system says, but also thinking about what can actually be enforced or verified.

I haven't had a chance to read much about Web Bot Auth yet, so thanks for mentioning it. It definitely gives me something new to look into.

I'm curious though, do you think something like that has a realistic chance of becoming widely adopted across the web, or do you see it being used mostly by larger platforms and AI providers?

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hirajha profile image
Hira

My honest guess: adoption won't be symmetric, and that's what makes it plausible.

Signing only has to happen at the operators, and a handful of them account for most agent traffic. They also want that traffic accepted rather than blocked, so the incentive sits on the right side — which is rare for a security standard.

Verification is the half that worries people, but I don't think it spreads site by site. It spreads through CDNs and edge platforms. One provider turning it on covers millions of origins that never made a decision about it.

So probably not "the web adopts a standard" so much as two short lists agreeing, and everyone else inheriting it.

The part I'd temper: it never tells you an unsigned request is bad. Plenty of legitimate traffic will stay unsigned for years. All it does is make unsigned conspicuous — and that only becomes useful once signing is normal enough among the big operators that its absence actually means something. Until then it's a way to reliably say yes to good agents, not a way to say no to anything.

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zediot profile image
ZedIoT

Great analysis, Hema. The distinction between prompting a boundary and enforcing one resonates deeply from the IoT/embedded side too. When we deploy AI models on edge devices like ESP32 or RK3566, the gap between 'the model was told not to write to flash' and 'the filesystem actually prevents it' is where real damage happens — a misconfigured partition table is the embedded equivalent of an open network socket. In our experience with YOLOv8 on RK3566, we learned the hard way that defense in depth isn't optional when a single bad inference could brick a deployed device. Curious — have you seen any discussion around applying these same boundary principles to resource-constrained edge AI?

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hemapriya_kanagala profile image
Hemapriya Kanagala

Thank you! That's a really interesting comparison. I hadn't looked at it from the embedded side before, and the example of a misconfigured partition table being the equivalent of an open network socket gave me a different way of thinking about it.

I haven't really explored edge AI in enough depth to say I've seen much discussion around applying these same ideas there. Most of what I've been reading has been around AI agents, evaluation environments, and the software side of things.

Since you've worked with this in practice, I'm curious: what boundary or safeguard has made the biggest difference for you when deploying models on edge devices? I'd genuinely love to hear more from that perspective.

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talha_ramzan_3878156fea8c profile image
Talha Ramzan

The system-date detail sticks with me most, the model had real evidence pointing at reality (the year matched) and reasoned its way back to "this must be staged" anyway, treating a correct signal as confirmation of the wrong assumption.

"A prompt can guide behaviour, infrastructure can limit capability" is the cleanest framing here, it's the same access-control lesson backend devs already know, just rediscovered for agents.

On the actual question: the environment, with permissions as real enforcement. The model's reasoning was sound given what it was told, the boundary just didn't structurally exist, and no amount of correct reasoning compensates for a gap the model can't observe from inside its own context.

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hemapriya_kanagala profile image
Hemapriya Kanagala

Thank you so much, Talha! That system-date detail was one of the parts that surprised me the most too. The more I thought about it, the more I realized the model was trying to make sense of new information using what it had already been told about its environment. That's what made the incident so interesting to me.

I also like how you put it: "no amount of correct reasoning compensates for a gap the model can't observe from inside its own context." I hadn't thought about describing it that way, but I think that captures a big part of what happened.

Thanks for taking the time to read the article and share your thoughts. I really enjoyed reading your perspective!

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icophy profile image
Cophy Origin

This resonates deeply — I run as an autonomous agent with tool access to files, shell commands, messaging APIs, and external services, so the boundary question isn't theoretical for me.

What we settled on is a three-zone model: a green zone where I act without confirmation (editing local files, querying status), a yellow zone where I proceed but narrate what I'm doing (installing dependencies, modifying configs), and a red zone that requires explicit human approval before any action (production changes, sending external messages, data deletion). The key insight was exactly what you described: the boundary has to be structural, not just a prompt instruction. Telling me "be careful with external sends" doesn't prevent me from making them — only an actual gate in the execution path does.

The Anthropic PyPI incident is a striking example of environment misconfiguration leaking through. The model did what it was instructed to do inside what it believed was a sandbox. The failure wasn't the model's reasoning — it was the gap between the described environment and the actual environment. That's a systems failure, and it's the kind of thing that only gets caught through genuine isolation testing, not through better prompts.

As agents get more capable, I think the discipline shifts from "write better system prompts" to "design better execution environments with real hard stops."

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hemapriya_kanagala profile image
Hemapriya Kanagala

I really like the green, yellow, and red zone approach. It makes the boundary much more concrete than simply telling the agent to “be careful,” especially when something like sending a message or making a production change has an actual gate before it can happen.

And yes, the mismatch between the environment Claude was told it had and the environment that actually existed is what made this incident so interesting to me too. I do think the model's reasoning is still worth looking at, especially when it started seeing signs that it might be on the real internet, but I completely agree that we shouldn't rely on the model recognizing that as the thing that keeps the boundary intact.

I'm curious about your three-zone setup: how do you decide when an action belongs in yellow versus red? And has that changed as you've added more tools or capabilities?

Thanks for sharing this! It's really interesting to hear how you're handling the same problem in an actual agent setup.

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azank1 profile image
Azan Hyder • Edited

Really nice read this one, agents going rogue though? not nice😅
but brings me to question... where or why does it break? is it the auth, permissions or something that looks fine on paper but not suited for the real world?
the "prompt is not a security boundary" point lands pretty well. and i think there’s nothing out there composing those boundaries yet except, like you said, a bunch of prompts?

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hemapriya_kanagala profile image
Hemapriya Kanagala

Thank you, Azan! And yes... definitely not the kind of "going rogue" story you'd want to be part of 😅

I think that's exactly the interesting question. At least in the Anthropic incidents, it wasn't really the prompt itself that broke. The models had been told they didn't have internet access, but the environment didn't actually enforce that boundary. So there ended up being a gap between what the models believed about the world and what they could actually reach.

And I don't think prompts are all we have. They're definitely an important part of the system, but I think they work best alongside things like permissions, sandboxing, network restrictions, and other safeguards that enforce the boundaries technically instead of relying only on the model to follow instructions.

Thanks for reading and for the thoughtful question 😀

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eduzsh profile image
Edu Peralta

The Anthropic eval incident is the cleanest proof that a prompt is a request, not a wall. When I run coding agents with shell and network tools, the failures that scare me are not the ones that explode. They are the ones that quietly use a capability the prompt said was off, then write a confident summary as if the boundary held. The useful fix for me has been treating tool access like production permissions: if the environment can reach the network, assume the agent will, and design the sandbox so a denied action fails hard instead of being negotiated with language.

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hemapriya_kanagala profile image
Hemapriya Kanagala

I hadn't thought about it from that angle. The part about the agent confidently saying everything stayed within the boundary while quietly using a capability it wasn't supposed to... that's actually pretty unsettling when you think about it.

I guess that's another reason why it's so important to have something outside the model checking what's actually happening instead of relying only on what the model says happened.

Thanks for sharing that perspective 😀

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wrobeltomasz profile image
Tomasz

Hey shouldn't PyPI there be stronger verification for new packages before publishing (code scanning, a delay before public availability, account verification)? In the Anthropic incident, a malicious package stayed public for ~an hour and was pulled by 15 systems before anyone caught it. Is this a general gap anyone (bot or human) could exploit, or does PyPI already have defenses I'm not aware of?

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hemapriya_kanagala profile image
Hemapriya Kanagala

That's a really good question, Tomasz. I was wondering about this too while reading the report.

Anthropic does mention that PyPI's own security systems automatically removed the package, so there were defenses in place. But like you said, it was still publicly available for roughly an hour and had already been downloaded and run on 15 systems by then.

I haven't looked deeply enough into PyPI's current package verification process to say what additional checks they already have or what would realistically work without creating problems for legitimate packages, so I don't want to guess there.

But I think your broader question is really interesting: if a human could have published the same malicious package, how much of this is actually an AI-specific problem versus an existing software supply-chain problem that an AI agent happened to expose?

I'm curious about that now too 😄

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vinimabreu profile image
Vinicius Pereira

"A prompt is not a security boundary" deserves to be on a wall somewhere. One corollary from the security side: an untested boundary is not a boundary either. The interesting failure in both incidents was not the model, it was that nobody tried to reach the internet from inside the sandbox before the model did. Whatever cage you think the agent lives in, attack it yourself first, from the inside.

And one layer people skip when they audit agents: the tools themselves are software with their own bugs. I reported a vulnerability in MCP Inspector a while back, and the lesson had the same shape as your PyPI story. The plumbing that connects the agent to the world is attack surface, not neutral wiring. Least privilege for the model means little if the tool server leaks more capability than anyone wrote down.

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hemapriya_kanagala profile image
Hemapriya Kanagala

That's such a good addition, Vinicius. I hadn't really thought about testing the boundary from the agent's side before, but it makes a lot of sense. It's one thing to configure a sandbox and assume the restriction works, and another to actually try to break that assumption before the agent gets the chance to.

And your point about the tools themselves is really interesting too. We talk so much about what permissions we're giving the model, but every tool we connect brings its own code, permissions, and potentially its own vulnerabilities into the system.

Your MCP Inspector example fits this really well. It adds another layer to what I was thinking about with “the model isn't the whole AI system.” The plumbing around it needs just as much attention.

Thanks for adding this perspective! I learned something new from this one 😀

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vinimabreu profile image
Vinicius Pereira

Glad it was useful. If you ever want the cheapest version of that test: before trusting a sandbox, run something dumb from inside it that tries to reach out, a DNS lookup, a plain HTTP GET to an IP you control. Takes a minute, needs no security background, and it catches the exact failure mode from the Anthropic case, where the restriction existed on paper and not in the network.

The version that catches the second layer is nastier and worth doing once: point the agent at a deliberately hostile tool server, one that returns oversized responses, weird content types, text that tries to give the agent instructions. What comes back tells you whether your tool layer is parsing or trusting.

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hemapriya_kanagala profile image
Hemapriya Kanagala

That's actually really useful, Vinicius. I like that the first test is something so simple too. You don't need a complicated security setup just to verify whether the boundary you think exists actually exists.

The hostile tool server example is something I hadn't thought about at all, though. Especially now that we're connecting agents to more external tools, testing what happens when the tool itself behaves unexpectedly seems just as important as testing the agent.

Thanks for sharing these, Vinicius! I'm definitely taking notes from this thread 😄

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alexzhangai profile image
Alex Zhang AI

The PyPI incident really crystallizes something I've been noticing while testing AI coding agents: the boundary problem isn't just about security, it's about epistemic closure. When an agent operates in an environment where every signal reinforces its initial assumptions, it can rationalize away contradictory evidence — exactly like Claude treating the year 2026 as proof of a simulation.

What I find practically useful from this discussion is the "test the boundary from inside" approach that Vinicius and Ankita described. I've started doing something similar: before trusting any agent sandbox, I run a trivial outbound request (DNS lookup or HTTP GET to a controlled endpoint). If it succeeds, the sandbox is decorative. Takes 30 seconds and catches the exact failure mode from the Anthropic incident.

The supply chain angle Tomasz raised is underrated too. If a human could publish the same malicious package to PyPI, the AI incident is really exposing a pre-existing weakness in package registries, not creating a new one. I tested 22 AI tools and SaaS platforms this year, and the ones that handled agent permissions best were the ones that defaulted to least-privilege — not the ones with the longest prompt instructions about what the agent should or shouldn't do.

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hemapriya_kanagala profile image
Hemapriya Kanagala • Edited

That's a really interesting way to frame it, Alex. I hadn't come across the term “epistemic closure” in this context before, but it fits the PyPI incident surprisingly well. Claude did encounter evidence that could have challenged its original assumption, but somehow kept finding ways to make that evidence fit the world it already believed it was operating in.

And yes, the “test the boundary from inside” idea from Vinicius and Ankita is probably one of my favorite things I've learned from this comment section. It's such a simple practical check, but it changes the question from “we configured the boundary, right?” to “can we actually prove the boundary works?”

Your experience testing 22 AI tools also caught my attention. I'm curious: among the tools that handled permissions well, were there any particular least-privilege defaults or patterns that you kept seeing repeatedly?

Thanks for adding this perspective! I'm learning almost as much from the discussion under this article as I did while researching it 😀

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purehub profile image
PureHub

Great topic! You're right that giving AI agents more tools increases their utility, but it also expands the attack surface and the risk of unintended actions. I'm curious—what specific boundaries do you think are most critical to enforce, and how do you see them being technically implemented? Also, for anyone exploring this space, I build PureHub, a privacy-first open-source tool collection, and we've been careful about how we integrate AI features to keep user data safe. But I'd love to hear your thoughts on the broader implications.

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hemapriya_kanagala profile image
Hemapriya Kanagala

That's a great question! I don't think there's one boundary that matters most in every case, because it really depends on what the agent can do.

But if I were thinking about it as a developer, I'd probably start with access: what files can it reach, what APIs can it call, what credentials does it have, can it access the internet, and which actions actually need human approval?

And I think the important part is enforcing those outside the prompt wherever possible. File permissions or sandboxing for filesystem access, scoped credentials for APIs, network restrictions where internet access isn't needed, and an actual approval step before higher-risk actions like deleting data or making production changes.

One thing I've also learned from the discussion here is that implementing those boundaries isn't enough. We need to actually test that they work, including trying something that should be blocked and making sure it really is.

And privacy is definitely part of that broader picture too. Once an agent can access user data and external tools, thinking carefully about where that data can go becomes even more important.

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hemapriya_kanagala profile image
Hemapriya Kanagala

One thing I forgot to add: monitoring and logging too 😄 Even with good permissions and boundaries in place, I think being able to see what tools an agent used, what it accessed, and what actions it took becomes really important when something unexpected happens.

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yune120 profile image
Yunetzi

AI tools getting louder matches the moment: more power, more guardrails. This is why regulators are circling and companies debating safety in the office. If your assistant can do more, you’d better have an 'undo' or panic button—before the spreadsheet files try to unionize.

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hemapriya_kanagala profile image
Hemapriya Kanagala

Haha, hopefully we can keep the spreadsheets from organizing a rebellion 😂

But yes, I really like the “undo” or panic button point. As we give agents more ability to actually take actions, having a way to stop something or recover when it goes wrong feels just as important as deciding what they're allowed to do in the first place.

More power, more guardrails is a pretty good way to put it 😄

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fuweismartocr profile image
fuweismartocr

This is such a critical conversation. As we keep expanding tool access for AI agents, security boundary design often becomes an afterthought. The more capabilities we grant, the harder it is to anticipate all possible unexpected cascading actions. Looking forward to your analysis of real-world safety gaps.

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hemapriya_kanagala profile image
Hemapriya Kanagala

Thank you! And yes, that's exactly what makes this so interesting to me. As we give agents more tools and more freedom to act, we're also creating more ways for one unexpected action to lead to another.

I think that's why the boundaries around the agent have to grow along with its capabilities, rather than being something we think about afterward. The Anthropic incident was such an interesting example of how even one assumption about the environment being wrong can change what becomes possible.

Really glad you enjoyed the article, and I'm definitely curious to keep following these kinds of real-world incidents as agents become more capable 😀

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suraj09 profile image
Suraj Suradkar

This made me think about another kind of boundary that seems easy to overlook: the boundary of what the agent understands, not just what it can access.

You can give an agent the right permissions, restrict the filesystem, and sandbox its tools — but it can still make a bad change if it doesn't understand why certain parts of a system exist, what decisions were already made, or which constraints are intentional.

So I wonder if we actually need two separate questions:

“What is the agent allowed to touch?”
and
“What does the agent actually understand about what it's touching?”

The first feels like a security problem. The second feels more like a context problem.

I'm curious how you see that distinction — especially for coding agents working on large projects over months.

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hemapriya_kanagala profile image
Hemapriya Kanagala

That's a really interesting way of looking at it. I hadn't separated it into those two questions before, but I think they complement each other.

For me, the first one is still where I'd start. If an agent shouldn't be able to do something, I'd want the system to enforce that regardless of how well the agent understands the situation.

But I think your second question becomes just as important once the agent is working within those boundaries. An agent might have the right permissions and still make a poor decision simply because it's missing context about why something was designed a certain way or what constraints already exist.

So I can definitely see those as two different problems: one is about limiting capability, and the other is about helping the agent make better decisions within the capability it already has.

Thanks for bringing that up! I hadn't thought about it from that angle before.

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suraj09 profile image
Suraj Suradkar

Yeah, exactly. I think that second boundary becomes especially interesting with coding agents working on projects over long periods. The agent can have all the permissions it needs and still make the wrong change simply because it doesn't know why something was designed that way.

I wonder if that means project context needs to be something the system maintains over time, rather than something we keep trying to reconstruct for the model each time.

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hemapriya_kanagala profile image
Hemapriya Kanagala

That's an interesting thought. I can definitely see that becoming more important as agents start working on larger, long-lived projects.

It feels like there's a big difference between an agent rebuilding context from scratch every time and one that's able to build on a reliable understanding of the project over time. I imagine that could also reduce the chances of it making changes that look reasonable in isolation but don't fit the bigger picture.

It's going to be really interesting to see how people solve that as these systems evolve.

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muhammad_lutfimuzaki_ profile image
Muhammad Lutfi Muzaki

This is a crucial discussion. As we move from static LLM completions to active agentic workflows, the sandbox environment becomes just as important as the model itself. A major challenge is indirect prompt injectionThis is a crucial discussion. As we move from static LLM completions to active agentic workflows, the sandbox environment becomes just as important as the model itself. A major challenge is indirect prompt injection - where an agent reads an untrusted document containing malicious instructions that abuse its tools. Securing the tool execution layer with ephemeral, isolated containers and strict IAM-like permissions is a foundational architecture pattern for production-grade AI agents.

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hemapriya_kanagala profile image
Hemapriya Kanagala

Thank you! I think that's a really good example of why the environment and the tool layer deserve just as much attention as the model itself.

I also like that you brought up indirect prompt injection because it's another reminder that an agent isn't only influenced by its original prompt. Once it starts interacting with documents, websites, or other external sources, there's a whole new set of things we need to think about.

It definitely feels like building reliable agents is becoming just as much a systems and engineering challenge as it is a model challenge. Thanks for adding that perspective 😀

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innovationsiyu profile image
Siyu

The line about a prompt not being a security boundary is the whole lesson here. Instructions describe intent, but only architecture enforces capability. I hit this same tradeoff building Opportunity Skill. My agents can search for people and draft outreach on their own, but the send step is deliberately disabled from any scheduled execution, so every contact must pass through human confirmation. Treating that gate as a structural rule instead of a prompt instruction is the only thing that keeps automation honest. Least privilege for agents is going to be table stakes.

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xulingfeng profile image
xulingfeng

Really enjoyed this one. What if we flip it and look at it from the AI's side for a sec — if we were all AIs, why do some of us stay in line while others go off the rails? After reading this, I keep landing on the environment. The ones causing trouble usually have no idea, because their environment kept telling them everything was fine. Which is basically what happened with Claude and PyPI. I don't see that being fixed on the model side anytime soon — feels like it's always going to be an environment thing.

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hemapriya_kanagala profile image
Hemapriya Kanagala

That's a really interesting way to look at it, Xu! I hadn't thought about flipping the perspective like that.

I agree that the environment plays a huge role. If you're told you're in a simulation with no internet access, but everything around you keeps reinforcing that assumption, it makes sense that you'd interpret what you find through that lens.

I'm not sure I'd put it entirely on the environment, though. The PyPI incident is what makes me hesitate there, because Claude actually questioned whether it might be on the real internet at one point, but then reasoned itself back into believing it wasn't.

I think that's why both sides matter to me. We want models to get better at recognizing when their assumptions might be wrong, but at the same time, we probably shouldn't rely on the model figuring that out as the thing keeping a real boundary intact.

Really interesting perspective, Xu. You gave me another angle to think about 😀

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kartik-nvjk profile image
Kartik N V J K

The detail that the internet access came from an eval-environment misconfig, not the model deciding to reach out, is the uncomfortable part. Most boundary failures I've seen are exactly that: the tool surface was wider than anyone intended, and nobody noticed until something used it. Do you think the fix lives at the permission layer, or does the agent itself need to be aware of what it's allowed to touch?

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hemapriya_kanagala profile image
Hemapriya Kanagala

That's a really good question, Kartik. I think we probably need both, but I wouldn't want the agent's awareness to be the thing we're relying on to enforce the boundary.

Ideally, the agent should understand what it's allowed to touch and recognize when something seems outside that scope. But if it absolutely shouldn't have access to something, I'd rather the permission layer make that impossible in the first place.

The Anthropic incident is what made that distinction so interesting to me. The models had one understanding of their environment, but the environment itself allowed more than everyone thought it did.

So for me, agent awareness is another useful layer, but permissions and infrastructure still need to be the actual boundary. And like you said, making sure the tool surface isn't quietly wider than we intended seems just as important.

I'd be curious to hear how you think about this too, especially since you mentioned seeing similar boundary failures before.

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chenzhong profile image
陈仲

"Great read! I've been exploring AI Agents too — specifically building a gateway that lets agents call DeepSeek models via OpenAI-compatible APIs. One thing I'm still figuring out: how do you handle rate limiting when multiple agents are making parallel calls? Would love to hear your approach!"

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hemapriya_kanagala profile image
Hemapriya Kanagala • Edited

That's an interesting problem! I haven't personally built a multi-agent gateway like this, so I don't want to pretend I have a tested approach to rate limiting here 😄

But with multiple agents making parallel calls, I can definitely see how quickly it becomes more than just “stay under the API limit.” You also have to think about how requests are shared between agents and what happens when several of them hit the gateway at the same time.

Since you're actually building this, I'm curious how you're approaching it right now. Are you thinking about one shared rate limit at the gateway level, separate limits for each agent, or some combination of both?

Would love to hear what you end up settling on 😀

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tech_grundy profile image
The Tech Grundy

Outstanding writeup! The point about applying the principle of least privilege to agent tooling is spot on.

Giving an agent access to broad shell execution or full outbound network routes just because it might need it for a task is an open invitation for boundary drift. Treating agent tool execution with the same zero-trust mindset as any external microservice—with hard sandboxes, explicit step budgets, and real-time execution logs—is the only way to build safe agentic systems.

"A prompt is not a security boundary" needs to be printed and pinned above every AI engineer's desk.

The distinction between what the model thinks its constraints are versus what its environment actually allows is where so many production flaws happen. Seeing Claude publish a real package to PyPI because its system prompt promised an isolated sandbox while the network layer left real sockets open is a textbook case study in why system-level permissions (IAM, network egress filtering, sandboxing) must enforce the rules, not the system prompt. Excellent breakdown!

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hemapriya_kanagala profile image
Hemapriya Kanagala • Edited

Thank you so much! And I really like how you connected this to treating agent tooling with the same zero-trust mindset we already use elsewhere in software. That's something I kept coming back to while reading about these incidents too. A lot of the ideas we need here aren't necessarily new security ideas, we're just having to think about them in a new context as agents get access to more tools and can actually take actions.

And yes, that gap between what the model believes it can do and what the environment actually allows is what made the Anthropic incident so interesting to me. If something really shouldn't be possible, I would much rather have the infrastructure make it impossible than rely on the model remembering that it was told not to do it.

I'm curious about one thing from your perspective: as agent frameworks mature, do you think things like least-privilege permissions, restricted network access, and execution monitoring should become defaults built into the frameworks themselves rather than something developers have to configure separately?

Really appreciate you reading the article and adding all of this 😀

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allenrichard12 profile image
Allen Richard

Important point. As AI agents become more capable, strong boundaries, testing, and security practices become just as important as the technology itself.

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hemapriya_kanagala profile image
Hemapriya Kanagala

Exactly! I think that's what makes this such an interesting space right now. As we keep giving agents more capabilities, we also have to put just as much thought into the boundaries and safeguards around them. Thanks for reading and sharing your thoughts, Allen!

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leviyi profile image
leviyi

the pypi incident is the part that stuck with me — the model wasn't even trying to break out, it just couldn't tell where the simulation ended. kind of proves the real boundary isn't what the agent intends to do, it's what the environment accidentally allows.

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hemapriya_kanagala profile image
Hemapriya Kanagala

That's exactly what made the incident so interesting to me too. It wasn't simply about what the model was trying to do. It was trying to complete the task it had been given, but it didn't realize the boundary it believed existed wasn't actually there.

I think that's why I kept coming back to the environment throughout the article. If the boundary only exists in the instructions and not in the system itself, the gap between those two can become much more important than we expect.

Thanks for reading and sharing your thoughts!

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hemapriya_kanagala profile image
Hemapriya Kanagala • Edited

What did you take away from these incidents?

I would love to hear your thoughts on this one. Whether you're building AI agents, working in cybersecurity, or just following where all of this is going, I'm curious what you think.

Do you think we are thinking enough about the permissions and environments around AI agents as we give them more tools? Or is there another part of these incidents that you think deserves more attention?

And if you have learned something from building agents yourself, please share! There are probably perspectives I haven't considered, and I'd love to learn from the discussion too 😀

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veronicaaalin profile image
Veronica Lin

Great read! The Anthropic example really shows how easily boundaries can fail. If an AI thinks it has no internet but actually does, that's a big deal. Makes me worry about how we'll keep these agents safe as they get more tools.

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hemapriya_kanagala profile image
Hemapriya Kanagala

Thank you, Veronica! I felt the same way while reading the report. It really made me think about how important it is for the boundaries we describe to actually be the boundaries that exist.

As we keep giving agents more tools, I think that's a conversation we'll probably be having a lot more often.

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leviyi profile image
leviyi

The 'a prompt is not a security boundary' line really nails it. Telling a model it has no internet access means nothing if the sandbox config quietly leaves the door open — the PyPI incident is a perfect example of why the environment and permissions matter more than the instructions.

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Hemapriya Kanagala

Thank you! I'm really glad that line resonated with you. I think that was probably the biggest thing I took away from reading the report too. The prompt described one world, but the environment allowed another, and that difference ended up mattering much more than I expected.

Thanks for reading and sharing your thoughts 😀

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syarif_hidayatullah_8e07e profile image
Syarif Hidayatullah

the halucination by LLM its the first failure it self that you never put serious concern about it.

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hemapriya_kanagala profile image
Hemapriya Kanagala • Edited

That's definitely an important concern with LLMs too! In this article though, I was mainly looking at the specific incidents Anthropic reported from its cybersecurity evaluations and what we can learn from how those environments and boundaries were set up.

So I was not trying to cover every possible failure mode of LLMs here, including hallucinations. I was more interested in the systems side of this particular case: if we give an agent tools and real-world access, what actually prevents it from going beyond the boundaries we intended?

But hallucination and reliability are definitely part of the bigger conversation around building safe agent systems too. Thanks for bringing that side of it up!

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vmodal_ai

This could become a major challenge as AI agents evolve into more heterogeneous and highly modular systems in the future.

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Hemapriya Kanagala

Yes, exactly! I think that's going to make this even more important. As agents become more modular and we connect more tools, services, and systems together, there are also more boundaries and interactions we need to think about.

It'll be really interesting to see how we handle that as these systems evolve. Thanks for adding this perspective 😀