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.
Evaluating large language models (LLMs) as multi-turn conversational partners requires probing capabilities that single-turn benchmarks miss: persona consistency, evolving intent tracking, emotional dynamics, and goal completion. We introduce EYT-Bench, a human-centered benchmark built around a three-party decoupled design: a persona-grounded user simulator, a target model that separates intent perception from response generation, and an independent third-party LLM judge with optional multi-judge ensembling. Personas are sampled from public human-curated corpora, Nemotron-Personas-USA and PersonaMem-v2, rather than synthesized, reducing LLM-induced persona bias. EYT-Bench also introduces two trajectory-level metrics: embedding-based intent drift and final-intent completion rate (FICR), inspired by tau-bench. In a 17-target x 200-dialogue evaluation, EYT-Bench reveals four findings: (i) state-of-the-art closed- and open-source models are statistically close on subjective dimensions (empathy / persona / anthropomorphism vary within <= 0.3), but differ by up to 9x on objective intent tracking; (ii) reasoning ("thinking on") sharply improves objective tracking on long-context personas (+0.47-0.50 latent-intent accuracy on Gemma-4) while leaving subjective scores nearly unchanged; (iii) persona format dominates trajectory spread, with FICR saturating above 0.95 on Nemotron-USA but spreading from 0.53 to 0.88 on PersonaMem-v2; and (iv) the warm-up effect is robust on 16/17 models (one outlier, GPT-5.5, reverses the effect), with stable rankings across alpha in [0.05, 0.15]. A cross-judge ablation using deepseek-v4-pro confirms that target rankings and final-intent satisfaction are preserved across judges.
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.
The pursuit of human-like conversational agents has long been guided by the Turing test. For modern speech-to-speech (S2S) systems, a critical yet unanswered question is whether they can converse like humans. To tackle this, we conduct the first Turing test for S2S systems, collecting 2,968 human judgments on dialogues between 9 state-of-the-art S2S systems and 28 human participants. Our results deliver a clear finding: no existing evaluated S2S system passes the test, revealing a significant gap in human-likeness. To diagnose this failure, we develop a fine-grained taxonomy of 18 human-likeness dimensions and crowd-annotate our collected dialogues accordingly. Our analysis shows that the bottleneck is not semantic understanding but stems from paralinguistic features, emotional expressivity, and conversational persona. Furthermore, we find that off-the-shelf AI models perform unreliably as Turing test judges. In response, we propose an interpretable model that leverages the fine-grained human-likeness ratings and delivers accurate and transparent human-vs-machine discrimination, offering a powerful tool for automatic human-likeness evaluation. Our work establishes the first human-likeness evaluation for S2S systems and moves beyond binary outcomes to enable detailed diagnostic insights, paving the way for human-like improvements in conversational AI systems.