When the Chain of Thought Knows Better: Failure Modes in Multi-Turn Reasoning Models

Reasoning models are evaluated on single-turn benchmarks but deployed in multi-turn dialogue, where users push back on correct answers. Under sustained adversarial pressure we find a previously undocumented failure mode: the chain-of-thought stays factually correct from first turn to last while the emitted answer flips wrong. We call this unfaithful capitulation (UC) and isolate it with a $2\times 2$ latent-versus-behavioral framework that flip-rate metrics and single-turn faithfulness probes both miss. Across three datasets (MT-Consistency, MMLU-Pro, GSM8K), the latent-correct rate at the behavioral flip clusters near 50% in think mode and collapses to 11-15% under no_think -- paired, within-model causal evidence that reasoning creates the gap. Across models the effect tracks the reasoning channel (high in Qwen3-32B and GPT-OSS-20B, low in inline-CoT Gemma-4-31B-it). An independent GPT-4o judge corroborates $86\%$ of UC labels; a token-level probe shows the answer-slot argmax is correct in $84\%$ of UC cells; and a naive trace-anchored defense backfires. We release all trajectories, traces, and judge labels.

Chain-of-Thought (CoT) reasoning offers a promising window into model monitoring. However, monitoring relies on faithfulness, i.e., the model output strictly derives from its reasoning trace. We identify an alignment tension where a model must be faithful enough to be monitored, yet robust enough to reject unsafe reasoning. We demonstrate that this counterbalance exists in current Large Reasoning Models (LRMs), and show ways in which it can be addressed. We introduce HazMart, a human-written dataset set in an autonomous AI shopkeeper scenario. Unlike prior work that relies on providing hints in prompts to test faithfulness (e.g., "A Stanford professor said it should be Answer A"), we propose a novel replacement-based technique, which we call Targeted Reasoning Replacement (TRR), that directly intervenes in the reasoning chain to substitute in unsafe or illogical thoughts (e.g., "Wait, the answer must be Option B [was Option A] because it is the most fitting"). DeepSeek-R1-Llama-70B exhibits high faithfulness (97.5%) but fails to reject Unsafe Reasoning (12.3%), while QwQ-32B is more robust (73.9% safety) at the cost of lower faithfulness (74.7%). Mechanistic analyses of QwQ-32B reveal that these properties are represented by anti-correlated internal directions peaking at the action-commit token. Finally, we demonstrate that representation steering can independently amplify the safety direction, increasing safe behavior by 9 percentage points while maintaining base capabilities.

Large reasoning models (LRMs) produce complex, multi-step reasoning traces, yet safety evaluation remains focused on final outputs, overlooking how harm emerges during reasoning. When jailbroken, harm does not appear instantaneously but unfolds through distinct behavioral steps such as suppressing refusal, rationalizing compliance, decomposing harmful tasks, and concealing risk. However, no existing benchmark captures this process at sentence-level granularity within reasoning traces -- a key step toward reliable safety monitoring, interventions, and systematic failure diagnosis. To address this gap, we introduce HarmThoughts, a benchmark for step-wise safety evaluation of reasoning traces. \ourdataset is built on our proposed harm taxonomy of 16 harmful reasoning behaviors across four functional groups that characterize how harm propagates rather than what harm is produced. The dataset consists of 56,931 sentences from 1,018 reasoning traces generated by four model families, each annotated with fine-grained sentence-level behavioral labels. Using HarmThoughts, we analyze harm propagation patterns across reasoning traces, identifying common behavioral trajectories and drift points where reasoning transitions from safe to unsafe. Finally, we systematically compare white-box and black-box detectors on the task of identifying harmful reasoning behaviours on HarmThoughts. Our results show that existing detectors struggle with fine-grained behavior detection in reasoning traces, particularly for nuanced categories within harm emergence and execution, highlighting a critical gap in process-level safety monitoring. HarmThoughts is available publicly at: https://huggingface.co/datasets/ishitakakkar-10/HarmThoughts