arXiv subjects

Kevin Ashley

Publications and source records attributed to Kevin Ashley.

8 recordsLinked to original sources

arXiv2026

DLawBench: Evaluating LLMs Through Multi-Turn Legal Consultation

Lawyer-client consultation is a critical starting point for legal services. Effective legal assistance hinges on eliciting sufficient and truthful information from clients in order to devise strategies that best protect their interests. This task requires Large Language Models (LLMs) not only to perform robust legal reasoning, but also to strategically elicit material facts through multi-turn interactions and effectively guide clients with diverse personalities. Yet existing legal benchmarks overlook this interactive capability. To fill this gap, we introduce DLawBench, a diagnostic benchmark for real-world legal consultation. Drawing on realistic client behavior, we characterize lawyer-client interactions into four types: Cooperative, Dependent, Withdrawn, and Adversarial. Using dialogues grounded in real cases, DLawBench evaluates whether LLMs can effectively conduct legal consultation under realistic conditions. DLawBench comprises 461 cases from Chinese and U.S. law, 5,532 paired fact entries, 3,411 inquiry rubrics, and 3,348 issue-resolution rubrics, and evaluates 26 representative LLMs. Systematic experiments show substantial headroom: the best-performing model, GPT-5.5, achieves only 0.562 on consultation-grounded legal reasoning. More importantly, DLawBench exposes both sycophancy in legal consultation and a paradox: models perform worse when clients need guidance most.

cs.CL↗

arXiv2026

Retrieval-Based Multi-Label Legal Annotation: Extensible, Data-Efficient and Hallucination-Free

Multi-label legal annotation requires assigning multiple labels from large, evolving taxonomies to long, fact-intensive documents, often under limited supervision. Parametric encoders typically require task-specific training and retraining when the label set changes, while prompting generative large language models becomes costly and degrades as the label space grows. We cast legal annotation as retrieval: we embed documents and label descriptions with a frozen retrieval model and predict labels via k-nearest neighbors in the embedding space, enabling updates by re-embedding and re-indexing rather than gradient-based backpropagation. Across three legal datasets (ECtHR-A, ECtHR-B, and Eurlex with 100 labels), retrieval achieves competitive accuracy and strong data efficiency; on Eurlex, Qwen-8B retrieval improves Macro-F1 from 40.41 (GPT-5.2, zero-shot) to 49.12 while reducing estimated compute by 20-30 times compared to fine-tuning. With only (N=100) training samples, retrieval nearly doubles Micro-F1 over hierarchical Legal-BERT on ECtHR-A (48.29 vs. 27.87). We also quantify a reliability failure mode of generative inference: GPT-5.2 hallucinates labels outside the provided taxonomy in 0.12-0.9% of test samples under deterministic decoding. In contrast, retrieval strictly respects defined label sets, eliminating hallucination by design. These results suggest retrieval-model-based annotators are a practical, deployable alternative for high-cardinality and rapidly changing legal label spaces.

cs.CL↗

arXiv2025

Do LLMs Truly Understand When a Precedent Is Overruled?

Large language models (LLMs) with extended context windows show promise for complex legal reasoning tasks, yet their ability to understand long legal documents remains insufficiently evaluated. Developing long-context benchmarks that capture realistic, high-stakes tasks remains a significant challenge in the field, as most existing evaluations rely on simplified synthetic tasks that fail to represent the complexity of real-world document understanding. Overruling relationships are foundational to common-law doctrine and commonly found in judicial opinions. They provide a focused and important testbed for long-document legal understanding that closely resembles what legal professionals actually do. We present an assessment of state-of-the-art LLMs on identifying overruling relationships from U.S. Supreme Court cases using a dataset of 236 case pairs. Our evaluation reveals three critical limitations: (1) era sensitivity -- the models show degraded performance on historical cases compared to modern ones, revealing fundamental temporal bias in their training; (2) shallow reasoning -- models rely on shallow logical heuristics rather than deep legal comprehension; and (3) context-dependent reasoning failures -- models produce temporally impossible relationships in complex open-ended tasks despite maintaining basic temporal awareness in simple contexts. Our work contributes a benchmark that addresses the critical gap in realistic long-context evaluation, providing an environment that mirrors the complexity and stakes of actual legal reasoning tasks.

cs.CL↗

arXiv2025

Thinking Longer, Not Always Smarter: Evaluating LLM Capabilities in Hierarchical Legal Reasoning

Case-based reasoning is a cornerstone of U.S. legal practice, requiring professionals to argue about a current case by drawing analogies to and distinguishing from past precedents. While Large Language Models (LLMs) have shown remarkable capabilities, their proficiency in this complex, nuanced form of reasoning needs further investigation. We propose a formal framework that decomposes the process of identifying significant distinctions between cases into three-stage reasoning tasks. Our framework models cases using factual predicates called factors, organizes them into a legal knowledge hierarchy, and defines verifiable rules for identifying distinctions, analyzing their argumentative support, and evaluating their significance. Through comprehensive evaluation of modern reasoning LLMs, we reveal a paradox: while models achieve high accuracy on surface-level reasoning (Task 1), performance degrades on hierarchical reasoning (Task 2: 64.82%-92.09%) and collapses on integrated analysis (Task 3: 11.46%-33.99%). Most strikingly, we find that models consistently expend more computational resources on incorrect responses than correct ones, suggesting that "thinking longer" does not always mean "thinking smarter." Our work provides a methodology for fine-grained analysis of LLM reasoning capabilities in complex domains and reveals fundamental limitations that must be addressed for robust and trustworthy legal AI.

cs.CL↗

arXiv2024

Using LLMs to Discover Legal Factors

Factors are a foundational component of legal analysis and computational models of legal reasoning. These factor-based representations enable lawyers, judges, and AI and Law researchers to reason about legal cases. In this paper, we introduce a methodology that leverages large language models (LLMs) to discover lists of factors that effectively represent a legal domain. Our method takes as input raw court opinions and produces a set of factors and associated definitions. We demonstrate that a semi-automated approach, incorporating minimal human involvement, produces factor representations that can predict case outcomes with moderate success, if not yet as well as expert-defined factors can.

cs.CL↗

arXiv2023

Question-Answering Approach to Evaluating Legal Summaries

Traditional evaluation metrics like ROUGE compare lexical overlap between the reference and generated summaries without taking argumentative structure into account, which is important for legal summaries. In this paper, we propose a novel legal summarization evaluation framework that utilizes GPT-4 to generate a set of question-answer pairs that cover main points and information in the reference summary. GPT-4 is then used to generate answers based on the generated summary for the questions from the reference summary. Finally, GPT-4 grades the answers from the reference summary and the generated summary. We examined the correlation between GPT-4 grading with human grading. The results suggest that this question-answering approach with GPT-4 can be a useful tool for gauging the quality of the summary.

cs.CL↗

arXiv2023

Argumentative Segmentation Enhancement for Legal Summarization

We use the combination of argumentative zoning [1] and a legal argumentative scheme to create legal argumentative segments. Based on the argumentative segmentation, we propose a novel task of classifying argumentative segments of legal case decisions. GPT-3.5 is used to generate summaries based on argumentative segments. In terms of automatic evaluation metrics, our method generates higher quality argumentative summaries while leaving out less relevant context as compared to GPT-4 and non-GPT models.

cs.CL↗

arXiv2022

Multi-granularity Argument Mining in Legal Texts

In this paper, we explore legal argument mining using multiple levels of granularity. Argument mining has usually been conceptualized as a sentence classification problem. In this work, we conceptualize argument mining as a token-level (i.e., word-level) classification problem. We use a Longformer model to classify the tokens. Results show that token-level text classification identifies certain legal argument elements more accurately than sentence-level text classification. Token-level classification also provides greater flexibility to analyze legal texts and to gain more insight into what the model focuses on when processing a large amount of input data.

cs.CL↗