An LLM-Based Agent for Legal Compliance Assessment: Architecture, Memory, and Evaluation in a Canadian and Quebec Context

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.

Large language model (LLM) agents increasingly perform commercial tasks that involve retrieving external content, such as images, and, where appropriate, reproducing that content. LLM agents should comply with the law, including copyright law. Presently, however, we lack adequate frameworks to assess whether they do so in practice. To that end, we introduce Copyright-Bench, a benchmark designed to evaluate LLM agents' compliance with copyright law. Copyright-Bench comprises realistic commercial tasks---website development, merchandise design, and pitch deck production---that involve agents selecting between public-domain content, the use of which is legal, and copyrighted content, the use of which is infringing in this setting. The evaluation introduces prompt variations that simulate different user preferences, as well as time pressure. Comparing state-of-the-art LLM agents against a human baseline, we find that: (1) agents select copyrighted works despite the availability of public-domain alternatives; and (2) for open-weight models, violation rates increase in response to certain user preferences and simulated time pressure.

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.