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Retrieval-based factuality evaluation, where LLM-generated claims are verified against evidence from authoritative medical corpora, has become the dominant paradigm for scalable hallucination detection in high-stakes clinical settings. Despite the urgency of reliable and transparent medical fact verification, most systems measure performance with aggregate metrics like F1, which obscure where and why failures occur. Existing RAG diagnostics require gold answers or annotated gold evidence, neither of which exists in this regime. We introduce two comprehensive taxonomies, grounded in a case study on the open-ended MedExpert dataset and 3 closed-ended datasets, decomposing failures into retrieval-stage errors along five quality dimensions, and verifier-reasoning errors into six consecutive steps. We adapt an automatic pattern induction pipeline using LLM-as-Judge to label evidence quality and classify verifier reasoning errors at scale, and then stress-test our findings across 4 retrieval methods and 6 frontier verifier models. Our analysis reveals that scaling model size, adding reasoning effort, expanding to authoritative web sources, and applying medical fine-tuning do not resolve these failure modes, demonstrating that they represent fundamental limitations of the retrieve-then-verify paradigm in open-ended medical settings rather than artifacts of outdated systems. We release our code and data at https://anonymous.4open.science/r/Medical_RAG_eval-4AB5 for the full reproducibility of our results.

Large language model (LLM) assistants increasingly help users with everyday activities that involve time-dependent constraints. However, users may not mention these constraints in later requests, requiring assistants to recognize and adjust their advice accordingly. To evaluate such capability, we introduce TASC (Temporal Action Safety in Conversation), a benchmark that evaluates whether LLMs apply time-dependent constraints when responding to conversational requests. TASC consists of 3,418 inputs derived from 128 templates, along with a separate set of 33 scenarios designed to compare models' ability to calculate elapsed time with their ability to apply that information. Across 13 models, assistants account for time-dependent constraints in only 30.5% of cases where the proposed action violates a rule, while rarely warning users unnecessarily. More importantly, models fail to apply these constraints in 62.1% of cases despite correctly calculating the elapsed time. Explicitly providing the timing resolves only about half of these failures, revealing a gap between temporal reasoning and its application in conversational advice.