Multi-Turn Dialogue Evaluation

Standard benchmarks report aggregate accuracy, but practitioners need to know which specific capabilities a model lacks. We introduce FailureScope, a behavioral-diagnosis method that clusters evaluation probes by their cross-model pass/fail patterns (leave-one-model-out, LOMO), and show it yields stable, interpretable failure taxonomies across three regimes usually studied separately: single-turn benchmarks, multi-turn dialogue, and adversarial agent attacks. On 2,664 single-turn tasks across 18 models, taxonomy-conditioned sampling reaches Kendall's tau = 0.81 at 50 tasks (versus 0.34 for random selection), and cross-model failure prediction reaches AUC 0.88. The same primitive recovers interpretable clusters on a 363-task multi-turn corpus and on 630 adversarial agent traces, where it exposes a meta-failure mode: a 73-100 percentage-point gap between LLM-judge ASR and real execution. Cluster cohesion remains strong across all three regimes, which we take as evidence that behavioral clustering is a portable diagnosis primitive that generalizes beyond any single benchmark. We release the pipeline, three annotated corpora, and the cross-regime taxonomies.

Multimodal large language models (MLLMs) demonstrate remarkable visual understanding, yet their reliability in interactive settings is severely undermined by hallucination snowballing: a phenomenon where initial errors amplify across conversational turns, leading to a collapse in coherence. This failure reveals a fundamental vulnerability where models progressively neglect visual grounding in favor of over-relying on polluted textual history. Existing benchmarks are predominantly confined to single-turn VQA, which fail to capture the complex dynamics of error propagation in long-horizon interactions. To address this, we introduce MM-Snowball, the first benchmark for fine-grained diagnosis of hallucination snowballing within dialogues. Extensive evaluation shows that our benchmark poses a significant challenge even to advanced MLLMs and reveals the inefficacy of existing mitigation methods designed for single-turn VQA. To counteract this degradation, we propose Conflict-Aware Visual Rectification (CAVR). This training-free method mitigates snowballing through a synergistic dual-mechanism that refreshes visual grounding at the representation level and rectifies output distributions at the logit level, effectively re-anchoring the model to visual facts. Experiments demonstrate that CAVR achieves state-of-the-art performance, offering a promising path toward more reliable interactive AI. Data and code are available at: https://frenkie-chiang.github.io/MM-Snowball

User satisfaction with AI assistants is highly personalized: the same response may satisfy one user but disappoint another depending on what each user expects and what they have asked for before. Existing automatic evaluation methods mostly measure generic response quality, making it difficult to judge whether a response satisfies a user at a specific turn. We study this problem as personalized turn-level user conversation satisfaction evaluation. We build a conversation satisfaction evaluator that combines compact user memories with target-turn context to produce satisfaction scores and dissatisfaction-oriented rationales. Meta-evaluation against human satisfaction annotations shows that personalized memory and post-hoc score calibration improve ordinal agreement and dissatisfied-turn detection over supervised, retrieval-based, and generic LLM-as-a-judge baselines. We further introduce PersTurnBench, a personalized turn-level user conversation satisfaction benchmark that uses the verified evaluator to assess generation models via replay. By holding the replay state fixed, PersTurnBench enables controlled comparison of generic generation models and memory-augmented personalized systems without new human labels for every candidate model. The evaluator and benchmark let researchers compare candidate generation models on personalized satisfaction without collecting new user feedback for every model.

Role-playing with large language models is fundamentally a session-level task, requiring agents to sustain character identity and interaction quality across extended multi-turn conversations. Yet existing evaluation and optimization methods remain largely turn-level, failing to capture long-horizon quality. We propose DynSess, a unified session-level framework for role-playing agents. DynSess-Eval scores complete dialogue sessions via rubrics targeting long-horizon behaviors. Leveraging its session-level rewards, we construct high-quality training trajectories through multi-turn lookahead search and train DynSess-Character with two complementary variants: DSPO (off-policy) and GSRPO (on-policy). Experiments show that DynSess-Eval aligns with human judgments substantially better than prior evaluators, and blind human evaluation further shows that DynSess-Character matches the strongest character model despite using substantially fewer parameters, while maintaining strong role consistency and interactive ability. Our dataset and code will be released to facilitate future research.

As interactive LLM-based applications are created and refined, model developers need to evaluate the quality of generated text along many possible axes. For simpler systems, human evaluation may be practical, but in complicated systems like conversational chatbots, the amount of generated text can overwhelm human annotation resources. Model developers have begun to rely heavily on auto-evaluation, where LLMs are also used to judge generation quality. However, existing LLM-as-a-judge benchmarks largely focus on simple Q&A tasks that do not match the complexity of multi-turn conversations. We introduce RankJudge, a benchmark generator for evaluating LLM-as-a-judge on multi-turn conversations grounded in reference documents. RankJudge creates pairs of conversations where one conversation has a single flaw injected into one turn. This construction allows paired conversations to be labeled unambiguously as better or worse, and precisely isolates failure categories to individual turns, enabling a strict joint correctness criterion for judging. We implement RankJudge across the domains of machine learning, biomedicine, and finance, evaluate 21 frontier LLM judges, and rank those judges via the Bradley-Terry model. Our formulation also allows ranking each conversation pair with difficulty ratings, which we use to dynamically curate the evaluation slice to reduce label noise, as confirmed via human annotation. We find that judge rankings are stable under partial observability, coarser correctness criteria, and an alternative random-walk rating algorithm.

Emotional intelligence (EI), the ability to perceive, understand, and respond appropriately to others' emotional states, is central to human communication, and increasingly important to assess as LLMs assume conversational roles in everyday life. Existing EI benchmarks rely on synthetic prompts, single-turn cases, or third-party annotation. These approaches do not directly measure how models infer and respond to a participant's emotional state over the course of a real conversation. We introduce AttuneBench, a benchmark grounded in 200 genuine multi-turn human-model conversations in which participants conversed with anonymized LLMs and provided turn-by-turn annotations of their emotional state, the model's behavior, and their preferred responses. Across 11 evaluated models, we find that model rankings on emotion recognition, behavioral classification, preference prediction, and judged response quality are largely independent, indicating that emotionally intelligent behavior decomposes into separable capabilities. Preference alignment and response-quality judgments are substantially more model-discriminating than emotion-label accuracy. These results indicate that emotionally intelligent behavior requires predicting what kind of response a specific user wants in context, a distinction that aggregate scoring can obscure and that single-turn or synthetic formats cannot directly capture across turns. AttuneBench provides a framework for assessing each of these capabilities and for diagnosing model-specific strengths and failure modes in emotionally salient conversation.

Accurate evaluation of conversational retrieval is pivotal for advancing Retrieval-Augmented Generation (RAG) systems. However, existing conversational retrieval benchmarks suffer from costly, sparse human annotation or rigid, unnatural automated heuristics. To address these challenges, we introduce MTR-Suite, a unified framework for auditing, synthesizing, and benchmarking retrieval. It features: (1) MTR-Eval, an LLM-based auditor quantifying alignment gaps in previous benchmarks; (2) MTR-Pipeline, a multi-agent system using greedy traversal clustering to generate high-fidelity dialogues at 1/400th human cost; and (3) MTR-Bench, a rigorous general-domain benchmark. MTR-Bench mimics production-style challenges (hard topic switching, verbosity), offering superior discriminative power. We make our code and data publicly available to facilitate future research at https://github.com/rangehow/mtr-suite.

Evaluating multi-turn dialogue systems remains challenging because response quality depends not only on the current prompt, but also on previously established entities, claims, and conversational commitments. Existing automatic evaluators, including LLM-as-a-judge frameworks and embedding-based metrics, largely rely on flat or turn-isolated representations, making them less effective at detecting long-range issues such as contradiction, topic drift, and entity inconsistency. To address this, we propose SKG-Eval, a quasi-deterministic and interpretable framework that models dialogue as an evolving Semantic Knowledge Graph (SKG) of entities, relations, and commitments across turns. The framework incrementally updates the graph through structured triple extraction and computes three complementary signals: (i) local relevance, measuring alignment with the current prompt and optional reference; (ii) historical consistency, evaluating how newly introduced information connects to prior conversational context using graph-based and embedding-driven signals; and (iii) logical coherence, assessed by a geometric contradiction engine that detects cross-turn conflicts without relying on NLI models or LLM judges. These signals are adaptively fused and aggregated into a length-invariant session score via recency-weighted trend analysis. Across multiple benchmarks, SKG-Eval achieves higher correlation with human judgments and substantially improves detection of long-range inconsistencies in extended conversations. In addition, the framework produces explicit contradiction certificates and deterministic scores for fixed inputs, enabling reproducible and auditable evaluation. Overall, our results suggest that structured externalized state tracking through semantic knowledge graphs provides a scalable alternative to implicit reasoning in LLM-based dialogue evaluators.

Users interacting with Large Language Models (LLMs) in a multi-turn conversation routinely refine their requests or pivot to new topics. LLMs, however, often miss these topic shifts and carry over irrelevant context from previous turns, leading to inaccurate responses. In this paper, we stress-test the multi-turn understanding of LLMs and study the following two sub-tasks: (1) detecting whether the user pivots or refines in the current turn, and (2) shortlisting relevant context from previous turns. To this end, we construct synthetic benchmarks based on real-world datasets from varied domains, as to simulate context shifts of different levels of difficulty. We then evaluate the zero-shot performance of ten LLMs (open-weight, closed-source and reasoning), and demonstrate that only some reasoning and strongly instructed LLMs are accurate in detecting pivots; open-weight LLMs struggle with the task and frequently carry stale context even with explicit cues; and all models suffer from a position bias. Based on the results, we discuss key takeaways for improving long-term robustness in multi-turn capabilities for LLMs.

Rankings produced by holistic LLM-as-a-judge scoring are sensitive to the bias of the chosen judge model. We show that switching to binary rubric scoring with multi-judge filtering removes this sensitivity: decomposing the judgement matters more than the judge model itself. To support this claim, we introduce Prosa, the first real user multi-turn Brazilian Portuguese chat benchmark: 1,000 WildChat conversations scored by three judges from three model families on 16 models. Under filtered rubric scoring the three judges agree on every one of the 16 ranks, whereas under holistic scoring they agree on only 7 of 16. Additionally, the rubric filtering pipeline increases the average score gap between neighbouring models by 47%, thereby improving Prosa's discriminative power. Evaluating a new model on Prosa costs approximately $2.1 when using Gemini 3 Flash as the judge. We release the benchmark and the filtering code to ensure that future models can be assessed under identical conditions. These artifacts also make our rubric-based scoring method reusable beyond Prosa, supporting other open-ended evaluation settings.

Language models are increasingly deployed in interactive settings where users reason about facts over time rather than in isolation. In such scenarios, correct behavior requires models to maintain and update implicit temporal assumptions established earlier in a conversation. We study this challenge through the lens of temporal scope stability: the ability to preserve, override, or transfer time-scoped factual context across dialogue turns. We introduce ChronoScope, a large-scale diagnostic benchmark designed to isolate temporal scope behavior in controlled multi-turn interactions, comprising over one million deterministically generated question chains grounded in Wikidata. ChronoScope evaluates whether models can correctly retain inferred temporal scope when follow-up questions omit explicit time references, spanning implicit carryover, explicit scope switching, cross-entity transfer, and longer temporal trajectories. Through extensive evaluation of state-of-the-art language models, we find that temporal scope stability is frequently violated in controlled multi-turn settings, with models often drifting toward present-day assumptions despite correct underlying knowledge. These failures intensify with interaction length and persist even under oracle context conditions, revealing a gap between single-turn factual accuracy and coherent temporal reasoning under sequential interaction. We make our dataset and evaluation suite publicly available at https://github.com/yashkumaratri/ChronoScope

In the maintenance of complex systems, fault trees are used to locate problems and provide targeted solutions. To enable fault trees stored as images to be directly processed by large language models, which can assist in tracking and analyzing malfunctions, we propose a novel textual representation of fault trees. Building on it, we construct a benchmark for multi-turn dialogue systems that emphasizes robust interaction in complex environments, evaluating a model's ability to assist in malfunction localization, which contains $3130$ entries and $40.75$ turns per entry on average. We train an end-to-end model to generate vague information to reflect user behavior and introduce long-range rollback and recovery procedures to simulate user error scenarios, enabling assessment of a model's integrated capabilities in task tracking and error recovery, and Gemini 2.5 pro archives the best performance.

Evaluating conversational AI systems that use external tools is challenging, as errors can arise from complex interactions among user, agent, and tools. While existing evaluation methods assess either user satisfaction or agents' tool-calling capabilities, they fail to capture critical errors in multi-turn tool-augmented dialogues-such as when agents misinterpret tool results yet appear satisfactory to users. We introduce TRACE, a benchmark of systematically synthesized tool-augmented conversations covering diverse error cases. Evaluation with state-of-the-art conversation evaluation frameworks reveals that all approaches remain far from ideal performance, demonstrating the fundamental difficulty of this benchmark.

As AI systems integrate into online spaces, differentiating them from humans in conversations is increasingly important. We present Inverse Turing Bench, a benchmark that evaluates LLMs and other models on their ability to differentiate humans and AI in multi-turn text. The benchmark provides a collection of paired dialogue transcripts, wherein one dialogue is between two humans and the other is between a human and an AI. The task is to correctly identify which dialogue is human-only vs. human-AI. We evaluated a preliminary set of models against this benchmark, and found that GPTZero, Claude Opus-4.6, and GPT-5.5 achieve the highest accuracy: 89.41%, 77.92%, and 75.94% respectively. Our results suggest that statistical approaches to detection have semantic blind spots, but semantic approaches are susceptible to persona-prompting. Our work speaks to the Inverse Turing Test and motivates human-AI differentiation as a critical capability for AI systems. Our live benchmark can be found at https://huggingface.co/spaces/roc-hci/Inverse-Turing-Bench-Leaderboard.