As Automatic Speech Recognition (ASR) is increasingly deployed in clinical dialogue, standard evaluations still rely heavily on Word Error Rate (WER). This paper challenges that standard, investigating whether WER or other common metrics correlate with the clinical impact of transcription errors. We establish a gold-standard benchmark by having expert clinicians compare ground-truth utterances to their ASR-generated counterparts, labeling the clinical impact of any discrepancies found in two distinct doctor-patient dialogue datasets. Our analysis reveals that WER and a comprehensive suite of existing metrics correlate poorly with the clinician-assigned risk labels (No, Minimal, or Significant Impact). To bridge this evaluation gap, we introduce an LLM-as-a-Judge, programmatically optimized using GEPA through DSPy to replicate expert clinical assessment. The optimized judge (Gemini-2.5-Pro) achieves human-comparable performance, obtaining 90% accuracy and a strong Cohen's $\kappa$ of 0.816. This work provides a validated, automated framework for moving ASR evaluation beyond simple textual fidelity to a necessary, scalable assessment of safety in clinical dialogue.

Large Language Models (LLMs) have shown impressive potential in clinical question answering (QA), with Retrieval Augmented Generation (RAG) emerging as a leading approach for ensuring the factual accuracy of model responses. However, current automated RAG metrics perform poorly in clinical and conversational use cases. Using clinical human evaluations of responses is expensive, unscalable, and not conducive to the continuous iterative development of RAG systems. To address these challenges, we introduce ASTRID - an Automated and Scalable TRIaD for evaluating clinical QA systems leveraging RAG - consisting of three metrics: Context Relevance (CR), Refusal Accuracy (RA), and Conversational Faithfulness (CF). Our novel evaluation metric, CF, is designed to better capture the faithfulness of a model's response to the knowledge base without penalising conversational elements. To validate our triad, we curate a dataset of over 200 real-world patient questions posed to an LLM-based QA agent during surgical follow-up for cataract surgery - the highest volume operation in the world - augmented with clinician-selected questions for emergency, clinical, and non-clinical out-of-domain scenarios. We demonstrate that CF can predict human ratings of faithfulness better than existing definitions for conversational use cases. Furthermore, we show that evaluation using our triad consisting of CF, RA, and CR exhibits alignment with clinician assessment for inappropriate, harmful, or unhelpful responses. Finally, using nine different LLMs, we demonstrate that the three metrics can closely agree with human evaluations, highlighting the potential of these metrics for use in LLM-driven automated evaluation pipelines. We also publish the prompts and datasets for these experiments, providing valuable resources for further research and development.

Despite the growing use of large language models (LLMs) in clinical dialogue systems, existing evaluations focus on task completion or fluency, offering little insight into the behavioral and risk management requirements essential for safety-critical systems. This paper presents MATRIX (Multi-Agent simulaTion fRamework for safe Interactions and conteXtual clinical conversational evaluation), a structured, extensible framework for safety-oriented evaluation of clinical dialogue agents. MATRIX integrates three components: (1) a safety-aligned taxonomy of clinical scenarios, expected system behaviors and failure modes derived through structured safety engineering methods; (2) BehvJudge, an LLM-based evaluator for detecting safety-relevant dialogue failures, validated against expert clinician annotations; and (3) PatBot, a simulated patient agent capable of producing diverse, scenario-conditioned responses, evaluated for realism and behavioral fidelity with human factors expertise, and a patient-preference study. Across three experiments, we show that MATRIX enables systematic, scalable safety evaluation. BehvJudge with Gemini 2.5-Pro achieves expert-level hazard detection (F1 0.96, sensitivity 0.999), outperforming clinicians in a blinded assessment of 240 dialogues. We also conducted one of the first realism analyses of LLM-based patient simulation, showing that PatBot reliably simulates realistic patient behavior in quantitative and qualitative evaluations. Using MATRIX, we demonstrate its effectiveness in benchmarking five LLM agents across 2,100 simulated dialogues spanning 14 hazard scenarios and 10 clinical domains. MATRIX is the first framework to unify structured safety engineering with scalable, validated conversational AI evaluation, enabling regulator-aligned safety auditing. We release all evaluation tools, prompts, structured scenarios, and datasets.