We introduce AutoMonitor-Bench, the first benchmark designed to systematically evaluate the reliability of LLM-based misbehavior monitors across diverse tasks and failure modes. AutoMonitor-Bench consists of 3,010 carefully annotated test samples spanning question answering, code generation, and reasoning, with paired misbehavior and benign instances. We evaluate monitors using two complementary metrics: Miss Rate (MR) and False Alarm Rate (FAR), capturing failures to detect misbehavior and oversensitivity to benign behavior respectively. Evaluating 12 proprietary and 10 open-source LLMs, we observe substantial variability in monitoring performance and a consistent trade-off between MR and FAR, revealing an inherent safety–utility tension. To further explore the limits of monitor reliability, we construct a large-scale training corpus of 153,581 samples and fine-tune Qwen3-4B-Instruction, to investigate whether training on known, relatively easy-to-construct misbehavior datasets improves monitoring performance on unseen and more implicit misbehaviors. Our results highlight the challenges of reliable, scalable misbehavior monitoring and motivate future work on task-aware designing and training strategies for LLM-based monitors.

Suicide remains a major global mental health challenge, and early intervention hinges on recognizing signs of suicidal ideation. In private conversations, such ideation is often expressed in subtle or conflicted ways, making detection especially difficult. Existing data sets are mainly based on public help-seeking platforms such as Reddit, which fail to capture the introspective and ambiguous nature of suicidal ideation in more private contexts. To address this gap, we introduce , a novel dataset of 1,200 test cases simulating implicit suicidal ideation within psychologically rich dialogue scenarios. Each case is grounded in psychological theory, combining the Death/Suicide Implicit Association Test (D/S-IAT) patterns, expanded suicidal expressions, cognitive distortions, and contextual stressors. In addition, we propose a psychology-guided evaluation framework to assess the ability of LLMs to identify implicit suicidal ideation through their responses. Experiments with eight widely used LLMs across varied prompting conditions reveal that current models often struggle significantly to recognize implicit suicidal ideation. Our findings highlight the urgent need for more clinically grounded evaluation frameworks and design practices to ensure the safe use of LLMs in sensitive support systems.