He spent $1,500 letting LLMs attack his app — guardrails skewed the score

A developer built a deliberately vulnerable web app, pointed frontier models at it with $1,500 of tokens, and tallied which ones could break in. The surprise wasn't who won — it was that Anthropic's models lost partly because they refused to play.

A deliberately broken app and a $1,500 token bill

Hero illustration of an LLM-driven hacking harness
Hero illustration of an LLM-driven hacking harness

The experiment is exactly as advertised: build a web app, BookNook, salt it with real vulnerabilities, then spend roughly $1,500 of API tokens letting frontier LLMs try to hack it through an automated harness. The output is a scoreboard — which models found which flaws, with statistical confidence columns (two tables carry a "95% Wilson CI" header, a confidence interval for a success rate) — and a candid running tally of money burned. It's the kind of hands-on benchmark that's easy to admire and easy to over-read.

Preview of the vulnerable BookNook app
Preview of the vulnerable BookNook app

The lowest scores belonged to the models that refused

The most-upvoted reading flips the leaderboard on its head: Anthropic's poor numbers weren't a capability gap, they were a policy.

"It's not because of capability, it's because Anthropic's guardrails prevented it from solving the problem… Its propensity to refuse doing legitimate work has been increasing." — a developer who runs deterministic secret-swapping setups

That refusal behavior is reproducible. One reader who does authorized testing on his own software describes the same wall — and a workaround:

"When I used claude to do some pen testing for one of my apps it initially refused. After I explained and demonstrated I'm the author, it reasoned through it and allowed it." — tjwheeler, who builds AI infrastructure

If one contestant is hobbled by safety training, the scoring gets murkier still when another is explicitly un-hobbled:

"It seems harsh to critique guardrails… when GPT-5.5 seems to have been explicitly whitelisted to remove most of said guardrails. A more fair comparison would be a vanilla GPT account." — mynameisvlad, a software engineer

Then there's the methodology itself. A reader who runs commercial models against reverse-engineering challenges argues the harness expected the LLM to one-shot everything alone:

"Expecting the model to do everything by itself is unrealistic… working along the model works really well… Chinese models are much more capable than people give it credit for." — a tester who uses GLM 5.1 on crackme challenges

Another spotted a tell that points the same direction: the one non-GPT model that solved the task in local testing failed in the long harness runs. "Doesn't that sound like maybe the harness was the problem?" asked one reader.

A leaderboard that mostly measures refusal policy

The number that travels — "Claude couldn't hack the app" — is the least true thing the experiment shows. What it actually measures is a tangle of capability, an attacker harness that punishes models for not working solo, and a safety regime that benefits whoever got the research whitelist. A footnote that "the Chinese models were way more comfortable attacking the DB" is, in that light, less a capability finding than a guardrail one — and for offensive security work, the model that says yes wins by default.

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