Large language models are rapidly being deployed as AI tutors, yet current evaluation paradigms assess problem-solving accuracy and generic safety in isolation, failing to capture whether a model is simultaneously pedagogically effective and safe across student-tutor interaction. We argue that tutoring safety is fundamentally different from conventional LLM safety: the primary risk is not toxic content but the quiet erosion of learning through answer over-disclosure, misconception reinforcement, and the abdication of scaffolding. To systematically study this failure mode, we introduce SafeTutors, a benchmark that jointly evaluates safety and pedagogy across mathematics, physics, and chemistry. SafeTutors is organized around a theoretically grounded risk taxonomy comprising 11 harm dimensions and 48 sub-risks drawn from learning-science literature. We uncover that all models show broad harm; scale doesn't reliably help; and multi-turn dialogue worsens behavior, with pedagogical failures rising from 17.7% to 77.8%. Harms also vary by subject, so mitigations must be discipline-aware, and single-turn "safe/helpful" results can mask systematic tutor failure over extended interaction.
Large language models are increasingly proposed as educational tutors, yet stronger task-solving ability does not necessarily imply stronger learning support. Motivated by recent calls to measure the social impact of NLP systems in practice, we study whether public LLM tutoring benchmarks distinguish learning-supportive behavior from mere answer production. We propose a lightweight diagnostic based on the gap between solving-oriented and pedagogy-oriented benchmark performance. Using public MathTutorBench leaderboard results, we show that these dimensions are only partially aligned: across eight publicly reported models, the correlation between solving and pedagogy composites is 0.421, and several models shift meaningfully in rank when evaluation moves from solving to pedagogy. We then analyze the public TutorBench sample and show that agency-relevant behaviors are explicitly encoded in benchmark rubrics, especially in active-learning settings that reward guiding questions, calibrated hints, and non-disclosive scaffolding. Together, these findings suggest that educational-impact evaluation should not treat task success as a sufficient proxy for learning support. We argue that public tutoring benchmarks can better support positive-impact evaluation by reporting solving-oriented and pedagogy-oriented scores separately and by making disclosure-sensitive, student-agency-preserving criteria more explicit.
Large Language Models (LLMs) have been widely explored in educational scenarios. We identify a critical vulnerability in current educational LLMs, pedagogical jailbreaks, where students use answer-inducing prompts to elicit solutions rather than scaffolded instructions. To enable systematic study, we unify and formalize safe, helpful, and pedagogical behaviors with a knowledge-mastery graph and introduce SHAPE, a benchmark of 9,087 student-question pairs for evaluating tutoring behavior under adversarial pressure. We propose a graph-augmented tutoring pipeline that infers prerequisite concepts from queries, identifies mastery gaps, and routes generation between instructing and problem-solving via explicit gating. Experiments across multiple LLMs show that our method yields significantly improved safety under two pedagogical jailbreak settings, while maintaining near-ceiling helpfulness under the same evaluation protocol. Our code and data are available at https://github.com/MAPS-research/SHaPE
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.