AnnoCaseLaw: Legal Annotation Benchmark of Civil Negligence

Applying computational methods to law at scale requires separating genuine legal reasoning from surface similarity. We study this through a concrete task: detecting implicit citations of the French Civil Code, where a court applies a statutory rule without naming it (a post-hoc question about the reasoning a court actually used). We release a benchmark of 1,015 passage-article pairs annotated by three legal experts. Our central finding is that their disagreement is itself informative: the third of cases the experts dispute are where models fail. Our best ensemble reaches an F1 score of 0.70 overall. Yet, two-thirds of its false positives fall on those disputed cases, a concentration that holds across all ten models we evaluate. Expert disagreement thus signals uncertainty in the task and in its gold label, which aggregate metrics hide. This should not block useful tools, however: reframed as top-$k$ ranking with multi-model consensus, the same signals reach 76% precision for the top-200 candidates of the benchmark without supervision.

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.

Two methodologies dominate current practices of benchmarking: rubric-based scoring evaluates items against predefined criteria, whereas comparative judgment elicits pairwise preferences between outputs. Although both methodologies are widely used, the choice between them is rarely justified. We release JudgmentBench, a benchmark of 30 real-world legal tasks, paired with 1,539 rubric scores and 1,530 pairwise preference judgments collected from practicing attorneys--including at major U.S. law firms--with substantial experience. The annotations constitute the first publicly available dataset in a high-expertise domain in which both supervision signals are elicited from the same experts on the same items. Using LLM-generated outputs at three constructed quality levels, we provide an initial empirical comparison: comparative judgments recover the intended quality ordering substantially better than rubrics under both a per-task rank-correlation metric (mean Spearman's rank correlation of 0.908 vs. 0.150, estimated difference = 0.758 [0.494, 1.021]) and a per-judgment pairwise win-rate metric (0.669 vs. 0.542, estimated difference = 0.127 [0.067, 0.186]), while requiring less than half the annotation time. The patterns hold for human annotators and LLM autograders. Beyond this initial comparison, the paired structure of the dataset supports a broader research agenda on how expert judgment should be elicited, aggregated, and used as supervision in domains without verifiable ground truth.