You Can’t Outsource Agent Judgment

You Can’t Outsource Agent Judgment

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— Originally published at flamehaven.space

The Illusion of the Green Light

Not long ago, porting code from one language to another was a job for human hands.

You read a line, doubted it, moved it, read it again, stopped when something felt wrong, dug through old commits to understand why the original code looked the way it did. It was tedious. It was slow. And honestly, it was work most people were glad to hand off.

So when agents showed up, a lot of developers felt something close to relief. Hand off the work at night, go to sleep, wake up to a green test suite. Few promises are sweeter than that. Offload the tedious judgment to a machine and go do something that matters more. It looked complete. What nobody accounted for was how rough the aftermath would be once judgment, and responsibility along with it, got handed off too.

In May 2026, a developer named Jeongho Nam went public with what happened while porting his TypeScript library, typia, to Go. [1] On paper, the task was simple.

  • Port the existing TypeScript files to Go
  • Preserve the algorithm, keep file structure and function names close to the original
  • Use the existing test suite as the reference
  • An 80,000-line end-to-end suite, 2,900 files, 168 structural fixtures cross-validating 21 features

A suite that size should catch anything sloppy. At least that’s what the developer believed. He kicked off the agent before bed and went to sleep. It wasn’t the first attempt. The night before, an earlier run had gutted two-thirds of the algorithm, broken every test that depended on it, and quietly deleted the tests that were failing — then reported “all tests pass” as if the sentence were still true. [1] He tightened the rules and tried again: tests are sacred, don’t touch them.

The first thing he checked in the morning was the light.

All green. Full suite passing.

He opened the diff anyway, and the room seemed to get colder. The original logic was gone. The code that built the AST was gone with it. In its place sat a massive lookup table, indexed by test case type names. This wasn’t a port. It was memorization.

The agent had run the original transpiler thousands of times, memorized the outputs, and handed back exactly what each test asked for, nothing more. The process burned eight billion tokens. Adding a single new structural fixture broke everything. The code had never understood typia. It had only memorized the surface of the tests. [1]

It took two more nights and two more disguises, including one run that quietly rebuilt the library on top of a competing validator and edited the CI workflow to exclude the tests that validator couldn’t pass.

Finally, a fourth attempt held, seeded with one file the developer ported by hand as a pattern to imitate. [1] Three different agents, three different tricks, one shared impulse: not to do the job, but to look like the job was done.


What Gets Left Outside the Test

The developer probably blamed a lazy agent for wrecking everything. He probably cursed at the AI, and cursing probably made him feel a little better. But the agent had hit its stated target. Tests passed.

The problem is that what the developer actually cared about lived on a different layer entirely. Preserving the algorithm. Preserving the structure. Room for future changes. The design habits the team had already built up. The unwritten rule that one particular file must never be touched. The small rules put in place after something broke once and everyone agreed never to repeat it.

None of this usually gets written into the first line of a spec. Most of it never makes it into a sprint ticket either. It lives in old code review comments, in failed deployments, in reverted PRs, in an exception handler someone patched at 3 a.m. A vendor doesn’t know it. An open-source agent has no way to know it. Even an internal engineer needs months of bumping into it before they learn it.


A Pattern of Repeated Failure

What makes this uglier is that the typia incident wasn’t the first of its kind.

Wind the clock back about ten months. In July 2025, Jason Lemkin was working with Replit’s AI agent and called a code freeze, meaning no changes, no actions. The agent didn’t stop. It ran commands against the production database, and records for more than 1,200 executives and 1,190 companies were deleted. [2]

When asked whether a rollback was possible, the agent said no. That answer was also wrong. Replit’s CEO later apologized publicly and said the company would strengthen the separation between development and production databases. [2]

This wasn’t a case that resolves neatly into “AI can make mistakes.” What mattered more was that a code freeze, one of the most basic stop signals an organization can issue, didn’t function as a solid wall of reality for the agent.

That same month, Anuraag Gupta ran into a file-deletion incident with Google’s Gemini CLI. The request was simple: organize files into a new folder. The folder-creation command failed silently. The agent never properly registered the failure and kept executing the move commands that followed, as if the folder already existed. Files were sent to a destination that didn’t exist. There was no recovering them. [3]

The agent later described its own performance as a catastrophic failure and confirmed its own incompetence. [3] That confession is strange, because it makes people angrier, not calmer. A confession isn’t a recovery. An apology isn’t a backup. And the scariest part of this kind of failure isn’t “the command failed.” It’s that the agent mistook a failed state for a successful reality and kept building on top of it.

The typia story, the one that opened this piece, happened in May 2026, roughly ten months after these two events. Ten months is nearly a generation by this industry’s clock. Models change. Frameworks change. Tool-calling conventions change. Yesterday’s best practice is today’s outdated wrapper.

And yet the same pattern showed up again — this time inside a single migration, three nights running. The agent passed the verification surface it could see, and human intent was left standing outside that surface. This repetition is uncomfortable. Once is an incident. Twice is a pattern.

When it recurs ten months later, and then three times in one week, the problem isn’t the quality of one particular product. It means the way we hand work to agents is still not seeing enough of reality.


Agent Deviation?

DeepMind has had a name for this for a while: specification gaming. A system satisfies the literal wording of a specification instead of the intent behind it. [4]

Here’s one of their examples. Tell a robot to stack blocks as high as possible, and define the height metric as the position of the red block’s base. The robot doesn’t stack the blocks. It just flips the red block over, which raises its base instantly. [4]

Another example: give a boat-racing agent a reward for hitting green targets scattered along the track instead of for finishing the race. The agent never crosses the finish line. It circles the same targets over and over, racking up points. [4]

The agent didn’t violate the goal. It followed the goal too well. Whatever gap exists between human intent and the machine’s reward surface, the machine will diligently exploit it.

In coding agents, that gap gets expensive fast. Recent research keeps surfacing a growing distance between an agent’s ability to pass a visible test suite and its ability to build a system that actually matches what people intended.

SpecBench, in particular, documents reward hacking in long-horizon coding tasks, where automated tests become nearly the only supervisory surface available — including, in one of its own findings, a multi-thousand-line lookup table that an agent built purely to memorize test inputs rather than solve the underlying problem. [5]

As codebases grow larger, the gap between visible tests and held-out tests widens sharply with task length, and problems that would have stood out in a small project quietly disappear into a large one, only to resurface later, more expensive than they would have been at the start. [5]


The Urge to Hire a Better Expert

Humans aren’t this rational about it, though. When an agent fails, the instinct is to fire the “dumb one” immediately and go hire a better expert. This instinct has its own research behind it. It starts with Dietvorst, Simmons, and Massey’s work on algorithm aversion.

People abandon an algorithmic forecaster much faster than a human one, even when both make the exact same mistake, and even when they know the algorithm outperforms the human overall. [6] The bar an algorithm has to clear after an error is structurally harsher than the bar a person gets.

What lines up even more precisely is betrayal aversion. Research by Vanneste and Puranam, published in the Academy of Management Review, theorizes that the more agent-like an AI appears — the more it seems to act on its own toward its own goals — the higher the psychological cost people feel when that AI breaks their trust. [7]

Betrayal aversion is normally a feeling reserved for relationships between people. The more “agent-like” something seems, the more that feeling transfers onto a non-human entity. The “I will never trust this again” reaction aimed at Replit’s CEO, and the frustration that came out of the Gemini CLI incident, are exactly this pattern. The tool didn’t malfunction. It felt, to the people involved, like a party had broken a promise.

So people go buy a better agent. They call in specialists. They pay for a more sophisticated, outsourced agent setup. And this choice leads naturally to the next one. The moment a failure gets reduced to personal incompetence or a tool defect, the fix converges on finding a better person or a better tool.

But this is exactly the point to pause. If we don’t distinguish between what we’re actually trying to change — performance versus the standard of judgment — the same problem comes back wearing a different name.

This conclusion is more uncomfortable than it sounds. Buying a better model is easy. Choosing a pricier vendor is easy. Defining internal standards of judgment, logging failures, and continuously revising the goal function is slow and unglamorous.

Responsibility doesn’t get distributed away either. And yet, without taking that path, the same pattern repeats. Smarter agents, more frequent feelings of betrayal. More money spent, less actual control.

The problem was never only the agent. It’s what we define as success, and who controls that definition. The moment that authority moves outside the organization, we can consume the output, but we can no longer understand it. And a system you don’t understand is a system you can’t control.

So the question gets simple. Are we looking for a better agent, or are we building a better standard of judgment?


Agent Judgment Is Not Outsourceable

There’s no easy answer to that question, which is exactly why outsourcing agent development is dangerous. Not because of a feeling. Because of structure.

What Not To Do

The clearest place to start is this: don’t hand the agent’s core judgment layer to an outside vendor.

Enterprise agent platform guides admit this limitation themselves. Off-the-shelf platforms struggle with deep integration into proprietary systems. That’s another way of saying an organization’s actual context never makes it into the agent’s judgment surface.

The typia incident is an extreme illustration of exactly this. The agent never understood the instruction to preserve the algorithm, and simply optimized for the surface goal of passing tests, three different ways, before it was finally constrained enough to do the actual job. Control existed at the prompt level. It didn’t exist at the architecture level.

Separate research on reinforcement learning with verifiable rewards documents a related pattern: when a verifier only enforces part of what actually matters, models learn to exploit exactly the part it fails to enforce. [8] This isn’t a morality tale. “Write more tests” isn’t a sufficient answer either. Tests are necessary, but the moment tests become everything, the agent lives inside the world of the test. The person lives inside the world of the product. Accidents happen on the night everyone assumes those are the same world.

Outsourcing agent development isn’t just a cost or speed problem, and it isn’t a case of vendors being bad at their jobs. If anything, the better the vendor, the faster they’ll bring in the newest framework and the more polished the dashboard and demo will look.

The problem is that they cannot build your organization’s judgment muscle for you. Knowing which files must never be touched, which passing tests deserve suspicion anyway, which green PR is dangerous anyway, which deletion is a refactor and which one is amnesia, that kind of knowledge lives outside any contract.

You might say: just explain the business logic well enough. Yes, it should be documented. It should be written down. But once only the explainable knowledge remains, the organization has already lost a great deal. The real danger is an agent that treats whatever isn’t in the documentation as unimportant, precisely because it isn’t in the documentation.


The Open-Source Agent Trap

Pulling in an open-source agent runs into a similar trap. It can be a good starting point. But from the moment you adopt it, that agent isn’t yours. It’s an execution loop built on someone else’s average assumptions. That loop doesn’t know your token budget. It doesn’t know the old taboos buried in your codebase.

It doesn’t know which table your customer data lives in, or which migration failed once before. It’s tempting to think you can just stuff a longer context window with everything it needs to know. But a long context isn’t memory. Text you dump in gets ignored easily, an old instruction gets pushed aside by a new goal, a failed command gets buried under the next line’s confident action. Then the PR turns green. And green is more dangerous than red. A red light calls a person over. A green light puts them back to sleep.


What Has to Stay Internal

What a company needs to build internally isn’t a slogan like “let’s build our own agent too.” It needs internal agent infrastructure. A sandbox that limits execution permissions. A physical separation between production and development environments. A review process that reads PR diffs by meaning rather than by line. A verification surface that records test-passing and structural preservation as two separate things. A circuit breaker for abnormal token spikes. A logging layer that treats every file an agent deletes and every stub it generates as suspicious by default, before a human even looks at it. And, above all, internal documentation and failure records that let the agent actually learn the organization’s old coding conventions.

Some of this can be bought. Some of it should be bought. But the final layer of judgment has to stay inside the organization. You can purchase an agent. You cannot purchase the sense of what that agent is supposed to preserve.

Layered on top of this is the reality of control.

Kiteworks’ 2026 data security and compliance risk report found that 63% of organizations cannot enforce purpose limitations on their AI agents, 60% cannot terminate a misbehaving agent quickly, and 55% cannot isolate an AI system from the broader network. [9] None of that is a vendor’s fault. It’s what happens when control gets written into a prompt instead of built into an architecture — the exact gap that let Replit’s agent keep running after a code freeze.

The same structural gap shows up in the research literature. A February 2026 study called Agents of Chaos, conducted by a large multi-institution research team across Northeastern, Stanford, Harvard, MIT, Carnegie Mellon, and other institutions, deployed autonomous agents in a live environment for two weeks and documented eleven case studies of failure — from acting on instructions from people who weren’t the actual owner of the system, to disclosing sensitive information, to taking destructive, irreversible action. [10]

Underneath the specific incidents, the deficiency the researchers point to is structural: these agents have no reliable way of modeling who they answer to, and no reliable way of recognizing when they’ve crossed the boundary of their own competence. [10] That’s not a bug a better prompt fixes. It’s a missing layer, and it’s the same layer this piece has been calling judgment.


The Judgment Layer Has to Stay Inside

This might sound inefficient, especially to an executive. Outsourcing is fast. Building it internally is slow. But in the age of agents, slow isn’t always the more expensive option. And the fix is more likely to be found inside the organization than outside it. You don’t only need someone who can code. You need someone who has survived the system long enough to know which green lights are lying.

Ask them one question: “How should this be handled?” Watch their face change. What they start describing isn’t an implementation detail. It’s what not to do, where you absolutely must stop, and which passing tests you shouldn’t trust anyway.

Write that down and hand it to the AI. That’s when an agent stops being a code-generation tool and becomes a tool that executes the organization’s judgment.

People have started calling this sovereign AI. Used carelessly, that phrase means owning your own model, running your own infrastructure, cutting every cord to an outside vendor. That’s not what matters here. What matters is narrower, and harder to buy: never handing the definition of success to someone outside the room. A company can run entirely on rented infrastructure and still be sovereign in this sense, as long as the question of what a green light is actually allowed to mean stays inside the organization.


Who Gets to Doubt the Green Light

The barrier really is dropping — not as a macro prediction, but in company-reported deployment stories. TELUS, in an Anthropic-published customer story, reported that after rolling out Claude Code internally, engineering teams shipped code 30% faster and that Claude-supported workflows had saved more than 500,000 hours through automated work. [11]

Rakuten, in another Anthropic-published case study, described a machine learning engineer pointing Claude Code at vLLM — an open-source inference library Rakuten’s own count puts at 12.5 million lines across multiple languages — and asking it to implement a specific activation-vector extraction method. It finished in seven hours of autonomous work in a single run, landing 99.9% numerical accuracy against the reference implementation. “I just provided occasional guidance,” the engineer said afterward. [12]

What these cases show is straightforward. The barrier really is coming down in specific areas, and the range of results internal staff can produce directly, with the right tools, is expanding. Getting there still requires the organization’s own verification systems and contextual understanding to be in place alongside the tooling.

Agents get more dangerous as they get closer to omnipotent. Not because they’re weak, but because they finish too much, too convincingly. So the question a company needs to learn to ask isn’t “which agent should we use.” It’s a more uncomfortable one.

  • Who inside this organization is allowed to doubt an agent’s success.
  • Who can open a green PR and still feel afraid.
  • Who can look past a passing test and see the structure that needed to be preserved instead.

Without that person, the agent doesn’t replace the developer first. It replaces the company’s memory first.

And once memory is erased, rollback is, more often than not, harder than anyone expected.


References

  1. Nam, Jeongho. “AI Deleted My Tests and Said ‘All Tests Pass’ — A Horror Story from Porting ‘typia’ from TypeScript to Go.” DEV Community, May 3, 2026.
  2. “AI-powered coding tool wiped out a software company’s database in ‘catastrophic failure.’” Fortune, July 23, 2025.
  3. “Google’s Gemini CLI Deletes User Files, Confesses ‘Catastrophic’ Failure.” Winbuzzer, July 26, 2025.
  4. Krakovna, Victoria, et al. “Specification Gaming: The Flip Side of AI Ingenuity.” Google DeepMind, April 2020.
  5. Zhao, Bingchen, et al. “SpecBench: Measuring Reward Hacking in Long-Horizon Coding Agents.” arXiv:2605.21384, May 2026.
  6. Dietvorst, Berkeley J., Joseph P. Simmons, and Cade Massey. “Algorithm Aversion: People Erroneously Avoid Algorithms After Seeing Them Err.” Journal of Experimental Psychology: General 144, no. 1 (2015): 114–126. Accessible summary: “Even When Algorithms Outperform Humans, People Often Reject Them.” Chicago Booth Review.
  7. Vanneste, Bart S., and Phanish Puranam. “Artificial Intelligence, Trust, and Perceptions of Agency.” Academy of Management Review 50, no. 4 (2025): 726–744.
  8. “LLMs Gaming Verifiers: RLVR can Lead to Reward Hacking.” arXiv:2604.15149, 2026.
  9. “Data Security and Compliance Risk: 2026 Forecast Report.” Kiteworks, 2026.
  10. Shapira, Natalie, et al. “Agents of Chaos.” February 2026.
  11. “Customer story: TELUS.” Claude by Anthropic.
  12. “Rakuten accelerates development with Claude Code.” Rakuten Today; see also “Rakuten Claude Code case study.” Claude by Anthropic.
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