Screwtape: Adversarial Transcript Editing for Monitor Red-Teaming

We introduce a red-teaming methodology that exposes harder-to-catch attacks for coding-agent monitors, suggesting that current practices may under-elicit attacks and overstate monitor performance. We identify three challenges with current red-teaming. First, mode collapse in attack generation, which we reduce with a novel attack taxonomy for broader coverage. Second, a conceive-execute gap: frontier LLMs can propose strong attack ideas or execute them, but not all at once. We mitigate this by decomposing attack construction into strategy generation, execution, and post-hoc trajectory refinement. Third, manual elicitation is costly to scale, which we address with our semi-automated red-teaming pipeline. Applied to BashArena, an AI control setting for tool-using coding agents, this pipeline produces MonitoringBench, a benchmark of 2,644 attack trajectories for evaluating monitor capabilities and failure modes. Our pipeline produces more diverse and stronger attacks: Opus-4.5 monitor's catch rate falls from 94.9% on elicited-only Opus attacks to 60.3% on our best refined attacks, with larger drops for several mid-tier monitors. Attacks optimized against three development monitors generalize to ten held-out monitors, with catch rates generally increasing with monitor capability. Using this benchmark, we provide a snapshot of the current monitor capabilities and find that frontier monitors often detect suspicious actions but fall for persuasion or fail to calibrate suspiciousness scores appropriately, suggesting tractable paths for improvement. MonitoringBench provides both a static benchmark for current tool-use monitors and a reusable methodology for refreshing these evaluations as agents and monitors improve.

Since autonomous coding agents generate complex behaviors at high-volume, we may want to use other LLMs to monitor actions to reduce the risk from dangerous misaligned behavior. To better understand the limitations of such monitors against the diverse attack strategies that a coding agent could use, we present SLEIGHT-Bench (Subtle Low-itEration Insight-Guided Harmful Transcripts), a benchmark of synthetic transcripts containing 40 attacks across 11 categories, each showing a coding agent covertly pursuing a harmful objective (e.g. weight exfiltration, credential theft, unmonitored rogue deployment). We find that 20 of 40 attacks are never caught by an Opus 4.6 monitor with extended thinking across 10 trials at a 1% false-positive rate, while the overall catch rate is 32%. We identify several evasion strategies such as exploiting model priors, user instruction ambiguity, and state manipulation, which facilitate creating attacks that evade frontier monitors. We also elicit stronger monitor performance using coding agents as monitors versus regular prompted monitors, and for some evasion strategies show improved catch rates with targeted monitor prompts. Our dataset and evaluation framework are available at https://github.com/safety-research/sleight-bench and https://huggingface.co/datasets/sleightbench/SLEIGHT-Bench.

Visible tests are a common gate for LLM-generated code, but passing them does not certify specification correctness. We study a deployment-like monitoring problem: after code has passed public tests, can a weaker LLM verifier identify the residual hidden bugs? We introduce Code Monitor Red Teaming, a monitor-red-teaming protocol that fixes a public-check information boundary while varying generator pressure, verifier scaffolding, and weak-to-strong capability. We instantiate it as CodeMonitorBench, spanning function-level, data-science, and workflow code. Across 71,000 generated candidates, 43,677 pass public tests and 23,081 of those fail hidden tests. Weak verifiers improve with scaffolding and model family, but still miss most hidden bugs at 5% false-positive rate. As a robustness stress test, adversarial public-test-overfit pressure lowers verifier AUROC and raises low-FPR miss rates in most cells. A GLM-5.1 verifier recovers part of the gap under the same evidence boundary; an inferability audit shows that remaining misses mix verifier failures with M1 evidence limits.