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RankJudge: A Multi-Turn LLM-as-a-Judge Synthetic Benchmark Generator

RankJudge is a novel benchmark generator for evaluating LLMs as judges in multi-turn conversations. It creates paired conversations where one has a single flaw injected into one turn, enabling unambiguous labeling and precise isolation of failure categories. Implemented across machine learning, biomedicine, and finance, it evaluated 21 frontier LLM judges and ranked them via the Bradley-Terry model. The approach also uses difficulty ratings to dynamically curate evaluations, reducing label noise.

SourcearXiv Computational LinguisticsAuthor: Zhenwei Tang, Zhaoyan Liu, Rasa Hosseinzadeh, Tongzi Wu, Keyvan Golestan, Jesse C. Cresswell

[2605.21748] RankJudge: A Multi-Turn LLM-as-a-Judge Synthetic Benchmark Generator

[Submitted on 20 May 2026]

Title:RankJudge: A Multi-Turn LLM-as-a-Judge Synthetic Benchmark Generator

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Abstract: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.

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Computation and Language (cs.CL)

Cite as: arXiv:2605.21748 [cs.CL]

(or arXiv:2605.21748v1 [cs.CL] for this version)

https://doi.org/10.48550/arXiv.2605.21748

arXiv-issued DOI via DataCite (pending registration)

Submission history

From: Zhenwei Tang [view email] [v1] Wed, 20 May 2026 21:20:01 UTC (814 KB)

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