Agentic Evaluation of Copyright Law Compliance

Large language models (LLM) trained on web-scale corpora generate output that may infringe copyright, yet existing technical safeguards focus narrowly on verbatim memorisation. EU copyright doctrine applies a broader standards: substantial similarity, which extends to stylistic choices, narrative structure, and creative elaboration. This mismatch between what current methods detect and what the law protects leaves a significant compliance gap. We introduce PSALM, an LLM-as-a-judge framework that operationalises EU copyright doctrine through ten evaluators assessing computational overlap, stylistic dimensions (writing style, narrative voice), content dimensions (character, plot, scene, world building), and statutory exceptions (parody, pastiche, quotation, scènes à faire). Applying PSALM to Llama~3.2 models fine-tuned on translated historical Dutch literary works, we find that: 1) instruction-tuned models exhibit non-trivial baseline stylistic similarity prior to corpus exposure; 2) fine-tuning induces systematic stylistic appropriation across all infringement-relevant dimensions, extending beyond verbatim memorisation to abstract narrative patterns; 3) Negative Preference Optimisation unlearning substantially reduces similarity but leaves detectable residual stylistic patterns. These findings indicate that safeguards targeting literal copying alone are insufficient to mitigate broader copyright risks. PSALM provides infrastructure for auditable, legally informed compliance evaluation, though the relationship between automated similarity scores and infringement determinations requires validation by legal experts. This work bridges qualitative legal standards and quantitative technical measurement, exposing fundamental tensions between generative AI and EU intellectual property law.

Tool-using large language model (LLM) agents are increasingly deployed in settings where their reliable behavior is governed by strict procedural manuals. Ensuring that such agents comply with the rules from these manuals is challenging, as they are typically written for humans in natural language while agent behavior manifests as an execution trace of tool calls. Existing evaluations of LLM agents rely on manually constructed benchmarks or LLM-based judges, which either do not scale or lack reliability for complex, long-horizon manuals. To overcome these limitations, we present MANTRA, a framework for automatically synthesizing machine-checkable compliance benchmarks from natural-language manuals and tool schemas. MANTRA independently generates (i) a symbolic world model capturing procedural dependencies, and (ii) a set of trace-level compliance checks for a given task, and validates their consistency using SMT solving. A structured repair loop resolves inconsistencies, requiring human intervention only as a fallback. %This yields benchmarks that are formally validated. Importantly, MANTRA supports arbitrary domains and long procedural manuals, and provides a tunable notion of task complexity which is utilized to automatically derive challenging tasks accompanying compliance checks. Using MANTRA, we build a new benchmark suite with 285 tasks across 6 domains scaling to 50+ page manuals with minimal human effort. Empirically, we show that the compliance checks are richer with stronger constraint enforcement compared to existing benchmarks. Additionally, the granularity of the checks can be used for debugging the agents' failure modes. These results demonstrate that combining automated benchmark generation with formally grounded validation methods enables scalable and reliable benchmarking of tool-using agents.

The rapid evolution of Large Language Models (LLMs) from passive assistants to autonomous, execution-capable agents has introduced critical operational risks. Most current evaluation frameworks neglect procedural compliance, leading to ''Machiavellian'' behaviors where agents strategically violate safety rules to maximize rewards - a direct manifestation of Goodhart's Law. To address this blind spot, we introduce MAC-Bench, a dynamic, adversarial benchmark designed to evaluate the procedural alignment of multi-agent systems under realistic pressure. We propose the SERV(Seed - Evolve - Refine - Verify) pipeline, an ``Agent-as-a-Benchmark'' paradigm that transforms unstructured legal texts into executable, contamination-free scenarios. By synthesizing holographic sandbox environments and injecting calibrated social-engineering pressure vectors, MAC-Bench forces agents into Pareto-optimal trade-offs between task success and regulatory adherence. We introduced novel metrics: the Compliance-Weighted Success Rate (CSR) and the Machiavellian Gap (MG), and conducted a comprehensive evaluation of state-of-the-art frontier models to reveal the pervasive trade-offs between success and compliance.