Language models offer a way to scale costly, labour-intensive expert annotation, but their ability to reproduce expert judgements remains uncertain. This is particularly challenging in law, where annotators must distinguish the reasoning supporting judicial decisions from other legally relevant discussion. We present AnnoCaseLaw as a densely annotated benchmark comprising $471$ U.S. civil-negligence court opinions with more than $12,000$ expert highlights across five annotation categories. We evaluate proprietary frontier, open-weight, legal-specialised, and decision models on their ability to reproduce these annotations. Models perform better on Facts and Outcome than on Application of Law to Facts, Procedural History, and Relevant Precedents. On Application of Law to Facts, proprietary frontier models achieve the strongest balance of reasoning coverage and precision, while the open-weight model Gemma 4 achieves comparable Macro-F1 to proprietary frontier models at a fraction of the estimated inference cost. Our findings highlight the importance of evaluating annotation coverage and cost alongside aggregate scores when assessing the feasibility of automated legal annotation.

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