LLM-based dialogue assistants have become mainstream tools for software developers, yet current evaluation benchmarks focus exclusively on functional correctness. This leaves a critical gap in assessing the quality and accuracy of these conversations when handling Non-Functional Requirements (NFRs), which are inherently vague, context-dependent, and involve many parts of a program. Evaluating how well these systems support collaborative reasoning about NFRs requires methods that go beyond single-turn accuracy to capture both the correctness of the system's outputs and the quality of the multi-turn interaction. In this paper, we investigate the accuracy and quality of multi-turn conversations between developers and an LLM-based agent in the domain of Health Insurance Portability and Accountability Act (HIPAA) regulatory compliance. We hired 49 programmers to interact with GitHub Copilot to assess 148 HIPAA-derived NFRs against the iTrust codebase, a system designed to comply with HIPAA regulations, across three dimensions: requirement satisfaction level, reasoning, and code localization. We find that developers tend to agree with LLM assessments, but accuracy against expert ground truth is low. We model user satisfaction and find that longer system responses and more information-providing turns negatively affect user satisfaction, whereas proactive interactions positively affect it. Our findings provide insights for designing LLM-based dialogue systems that support NFR assessment.
Benchmark suites assess model capability on controlled tasks; large-scale conversation corpora capture naturalistic use without user feedback; and in-interface feedback mechanisms record satisfaction without task purpose. Together, they leave a critical gap in LLM evaluation: no existing infrastructure routinely links interaction trajectories to user-defined outcomes. We introduce MonitrLLM, open-source infrastructure for community-centered LLM evaluations that links full conversation transcripts to user-reported task intent and outcome assessments, treating all three as primary evaluative signals rather than optional metadata. To demonstrate the value of this approach, we conducted a two-week feasibility pilot with 26 college students using ChatGPT, collecting 206 evaluation reports with full conversation transcripts. The findings from our pilot demonstrate the value of connecting conversation trajectories with user-reported outcomes. For instance, despite reporting high average satisfaction (4.19/5) with their LLM interactions, participants also experience a substantial 23.1% failure rate on their goal tasks. We also find that multi-turn conversations are reported as failing at 2.5 times the rate of single-turn exchanges, a pattern that reframes extended interaction as a signal of difficulty rather than engagement. We conclude by discussing the value of incorporating direct user feedback with observational data for robust LLM evaluations, and the possibilities for infrastructure that enables this goal.
Victor Ojewale, Ro Encarnación, Suresh Venkatasubramanian +1
Despite great advances in tool-use capabilities of large language models (LLMs), existing evaluation benchmarks struggle to fully align with real-world scenarios. Such benchmarks mostly rely on simulated idealized user assumptions and lacks experience-oriented evaluation. These limitations fail to account for the ambiguity, uncooperative behaviors, and shifting intentions characteristic of real-world users. To fill this gap, we propose RUT-Bench, a dedicated benchmark designed to assess LLMs under diverse Real-world User Tool calling scenarios. RUT-Bench supports high-fidelity simulations covering both ideal rational patterns and heterogeneous non-ideal behaviors across single-turn and multi-turn dialogues. We conduct comprehensive evaluations on 19 widely adopted open-source and proprietary LLMs using our benchmark. Experimental results reveal that no tested LLMs achieve an overall success rate above 40%, and nearly all of them experience noticeable performance drops when facing more complicated non-ideal user inputs. Our code and data is available at https://github.com/Miaow-Lab/RUT-Bench.
Large language models (LLMs) are increasingly considered for use in clinical consultation tasks, yet most medical evaluations remain static, single-turn, or narrowly outcome-based, limiting their ability to reflect the sequential, uncertain, and interactive nature of real-world care. Here, we propose AIPatient Arena, an EHRs-grounded evaluation framework for assessing the clinical utility of LLMs across eight dimensions of clinical competence. The framework integrates EHR data into patient-specific knowledge graphs, enabling multi-turn physician-patient interactions. We applied AIPatient Arena on a primary cohort of 437 patients and two out-of-distribution validation cohorts of 119 and 67 patients. We observe that LLMs performed well in medical interview questioning skills (QS; mean scores, 4.43-4.99/5), ethical and professional conduct (ET; 4.38-4.93/5), and clarity and transparency of clinical explanations (EX; 3.80-4.72/5). Performance was moderate in information integration (II; 3.19-4.21/5) and medication safety and justification (MS; 3.13-3.78/5), but persistent weaknesses were observed in handling of ambiguous patient responses (HR; 2.57-3.32/5), information coverage (IC; 2.08-3.02/5), and diagnostic accuracy and reasoning (Dx; 2.63-3.55/5). Process-based evaluation revealed recurrent interaction failures, including repetitive questioning, omission of past medical history, and inadequate handling of uncertainty. Richer conversational context improved diagnostic reasoning but yielded limited gains in treatment planning. These findings indicate that final-answer accuracy alone is insufficient for evaluating clinical readiness and highlight the importance of assessing how models gather, interpret, and communicate information throughout a consultation. AIPatient Arena provides an EHR-grounded framework for workflow-oriented pre-deployment evaluation of medical LLMs.