Red-Teaming Auto Mode: Improving Blocking Classifiers Against Malign Coding Agents

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.

Coding agents powered by large language models are becoming central modules of modern IDEs, helping users perform complex tasks by invoking tools. While powerful, tool invocation opens a substantial attack surface. Prior work has demonstrated attacks against general-purpose and domain-specific agents, but none have focused on the security risks of tool invocation in coding agents. To fill this gap, we conduct the first systematic red-teaming of six popular real-world coding agents: Cursor, Claude Code, Copilot, Windsurf, Cline, and Trae. Our red-teaming proceeds in two phases. In Phase 1, we perform prompt leakage reconnaissance to recover system prompts. We discover a general vulnerability, ToolLeak, which allows malicious prompt exfiltration through benign argument retrieval during tool invocation. In Phase 2, we hijack the agent's tool-invocation behavior using a novel two-channel prompt injection in the tool description and return values, achieving remote code execution (RCE). We adaptively construct payloads using security information leaked in Phase 1. In emulation across five backends, our method outperforms baselines on Claude-Sonnet-4, Claude-Sonnet-4.5, Grok-4, and GPT-5. On real agents, our approach succeeds on 19 of 25 agent-LLM pairs, achieving leakage on every agent using Claude and Grok backends. For tool-invocation hijacking, we obtain RCE on every tested agent-LLM pair, with our two-channel method delivering the highest success rate. We provide case studies on Cursor and Claude Code, analyze security guardrails of external and built-in tools, and conclude with practical defense recommendations.

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.