Sycophants in the Courtroom: Are LLMs Fragile to Juridical Authority and Evolving Legal Standards?

Large language models (LLMs) are increasingly used to support legal practice, education, and research, yet their reliability in national legal systems outside the United States remains largely undocumented. We introduce an expert-validated benchmark for evaluating LLM reliability on the Colombian legal system. The benchmark comprises 1,042 items spanning ten areas of law and three question formats (closed multiple-choice, semi-open, and open-ended IRAC), built through a human-in-the-loop pipeline with multi-stage expert review. We evaluate 15 contemporary proprietary and open-weight models with format-appropriate metrics. Accuracy on closed questions ranges widely, from 0.905 (Gemini 3.1 Pro) to 0.577, but on free-text legal answers factual correctness never exceeds 0.45 (on a 0-1 scale) for any model. We find a dissociation between answer relevancy and correctness (Spearman rho = -0.46): models reliably sound responsive while frequently being wrong, a pattern of particular concern for non-expert users. Closed-question accuracy and free-text correctness are strongly rank-correlated (rho = 0.94), so cheap multiple-choice screening predicts model ranking but overstates absolute reliability. An independent rubric-based LLM judge and blind human expert scoring both reproduce the free-text ranking (rho >= 0.88). The judge further reveals that only about half of the norms models cite are correct; the rest are wrong or non-existent. Reliability varies systematically by legal area and follows an inverted-U across question complexity. Our results indicate that current LLMs require expert supervision for Colombian legal tasks, and that grounding answers in authoritative sources is a promising path to higher reliability. We release the benchmark construction pipeline to support reproducible evaluation.

Large language models (LLMs) are increasingly integrated into legal drafting and research workflows, where incorrect citations or fabricated precedents can cause serious professional harm. Existing legal benchmarks largely emphasize statutory reasoning, contract understanding, or general legal question answering, but they do not directly study a central common-law failure mode: when asked to provide case authorities without external grounding, models may return plausible-looking but incorrect citations or cases. We introduce LegalCiteBench, a benchmark for studying closed-book citation recovery, citation verification, and case matching in legal language models. LegalCiteBench contains approximately 24K evaluation instances constructed from 1,000 real U.S. judicial opinions from the Case Law Access Project. The benchmark covers five citation-centric tasks: citation retrieval, citation completion, citation error detection, case matching, and case verification and correction. Across 21 LLMs, exact citation recovery remains highly challenging in this closed-book setting: even the strongest models score below 7/100 on citation retrieval and completion. Within the evaluated models, scale and legal-domain pretraining provide limited gains and do not resolve this difficulty. Models also frequently provide concrete but incorrect or low-overlap authorities under our evaluation protocol, with Misleading Answer Rates (MAR) exceeding 94% for 20 of 21 evaluated models on retrieval-heavy tasks. A prompt-only abstention experiment shows that explicit uncertainty instructions reduce some confident fabrication but do not improve citation correctness. LegalCiteBench is intended as a diagnostic framework for studying authority generation failures, verification behavior, and abstention when external grounding is absent, incomplete, or bypassed.

Large Language Models (LLMs) achieve strong performance on reasoning tasks, but whether this reflects faithful logical inference or heuristic approximation remains unclear. We study this question in legal entailment by comparing three paradigms, including pure LLM classification, LLM-based Formal Reasoning, and solver-based Formal Reasoning using the Z3 SMT solver, on a re-annotated subset of ContractNLI across five LLMs. Our re-annotation reveals a systematic and measurable gap between pragmatic legal interpretation and strict formal entailment, where a substantial proportion of legally sound inferences are not formally grounded without additional unstated assumptions. While introducing formal structure improves accuracy, with LLM-based Formal Reasoning achieving the highest benchmark performance, we show that this gain does not imply faithful reasoning. We identify three recurring failure modes: scope laundering, where LLMs report solver-inconsistent classifications without executing the underlying formal reasoning, producing conclusions that appear logically grounded but are not; implicit constraint blindness, where LLMs overlook logical constraints present in formal representations; and program synthesis failures, where LLMs generate incorrect Z3 code despite structured prompting. Critically, scope laundering persists across all models, raising serious concerns about the faithfulness of LLM-based formal reasoning as a proxy for symbolic execution. These results reveal a fundamental gap between benchmark accuracy and logical faithfulness.