Monitor Jailbreaking: Evading Chain-of-Thought Monitoring Without Encoded Reasoning

Chain-of-thought (CoT) monitoring is a promising tool for detecting misbehaviors and understanding the motivations of modern reasoning models. However, if models can control what they verbalize in their CoT, it could undermine CoT monitorability. To measure this undesirable capability -- CoT controllability -- we introduce the CoT-Control evaluation suite, which includes tasks that require models to solve problems while adhering to CoT instructions, e.g., reasoning about a genetics question without using the word 'chromosome'. We show that reasoning models possess significantly lower CoT controllability than output controllability; for instance, Claude Sonnet 4.5 can control its CoT only 2.7% of the time but 61.9% when controlling its final output. We also find that CoT controllability is higher for larger models and decreases with more RL training, test-time compute, and increased problem difficulty. CoT controllability failures extend even to situations in which models are given incentives (as opposed to direct requests) to evade CoT monitors, although models exhibit slightly higher controllability when they are told they are being monitored. Similarly, eliciting controllability by adversarially optimizing prompts does not meaningfully increase controllability. Our results leave us cautiously optimistic that CoT controllability is currently unlikely to be a failure mode of CoT monitorability. However, the mechanism behind low controllability is not well understood. Given its importance for maintaining CoT monitorability, we recommend that frontier labs track CoT controllability in future models.

Chain-of-thought (CoT) monitoring is one of the most promising tools we have for detecting model misbehavior, but its effectiveness depends on models faithfully externalizing their reasoning. Motivated by this vulnerability, we study whether monitor-aware models are capable of obfuscating their reasoning to evade detection. We use synthetic document finetuning to expose eight models to realistic pre-training-style documents describing a CoT monitor and find that monitor-aware models consistently achieve higher rates of undetected misbehavior compared to unaware controls. This effect is weaker but still present on a harder agentic task. We also show that CoT controllability, a model's ability to reshape its own reasoning trace under an imposed constraint, is closely correlated with obfuscation success across the eight models studied ($r=0.800$, $p=0.017$). Monitor-aware models placed under equal reinforcement learning optimization pressure also learn to reward-hack without triggering a CoT monitor substantially faster than unaware controls. Together, these results suggest that knowledge of monitoring combined with high CoT controllability poses a risk to CoT-based monitoring.

Can reasoning models trick chain of thought (CoT) monitors and perform hidden computation without revealing it in their thinking traces? We show that the answer depends on the underlying task difficulty and the model size. Simple computations can be performed covertly; however, beyond a threshold depending on model size, successfully solving the task necessarily leaks a near-linear amount of information about the covert task input into the CoT. Therefore, sufficiently complex hidden computation always leaves an information-theoretic footprint. However, concerningly, this leakage need not be readable: Under plausible cryptographic assumptions, even a one-layer Transformer can encrypt its reasoning online so that no polynomial-time monitor can extract information about the hidden computation. Overall, our theoretical and empirical results provide a holistic view of both the opportunities and the limitations of CoT monitoring.