Scientific inquiry involves iterative cycles of exploration, hypothesis generation, and reasoning over observations to uncover relationships in complex systems. Large language models (LLMs) have demonstrated strong capabilities in several components of this process, including inductive reasoning, hypothesis generation, and data analysis. However, prior work typically evaluates these abilities in isolation, leaving open how models integrate them across a full inquiry cycle. In this work, we introduce a framework for evaluating LLMs’ inquiry capabilities in a unified, interactive setting. We extend the Countdown task to a mathematical environment where an agent probes the system by manipulating variables, collecting observations, and inferring relationships between them. This setup enables analysis of exploration strategies, causal discovery, and hypothesis refinement during inquiry. Across seven LLMs and multiple prompting strategies, our experiments reveal limited inherent inquiry capabilities and low success rates in discovering the underlying expressions. However, structured guidance inspired by educational scaffolding significantly improves performance. Our findings highlight current limitations of LLMs in strategic exploration and iterative hypothesis refinement, and show how simple guidance strategies developed for human learners in inquiry learning can support more effective inquiry behavior.

Large Language Models (LLMs) are increasingly used in education, yet their default helpfulness often conflicts with pedagogical principles. Prior work evaluates pedagogical quality via answer leakage–the disclosure of complete solutions instead of scaffolding–but typically assumes well-intentioned learners, leaving tutor robustness under student misuse largely unexplored. In this paper, we study scenarios where students behave adversarially and aim to obtain the correct answer from the tutor. We evaluate a broad set of LLM-based tutor models, including different model families, pedagogically aligned models, and a multi-agent design, under a range of adversarial student attacks. We adapt six groups of adversarial and persuasive techniques to the educational setting and use them to probe how likely a tutor is to reveal the final answer. We evaluate answer leakage robustness using different types of in-context adversarial student agents, finding that they often fail to carry out effective attacks. We therefore introduce an adversarial student agent that we fine-tune to jailbreak LLM-based tutors, which we propose as the core of a standardized benchmark for evaluating tutor robustness. Finally, we present simple but effective defense strategies that reduce answer leakage and strengthen the robustness of LLM-based tutors in adversarial scenarios.