Large language models have strong potential for use in intelligent tutoring systems, but they often fail to follow effective pedagogical strategies, such as guiding students without revealing final answers. We study the application of a two-stage alignment pipeline for math mistake remediation, combining supervised fine-tuning on tutoring dialogs with Direct Preference Optimization on synthetic preference pairs. We construct a dataset that integrates existing tutoring corpora with synthetic data generated along pedagogical dimensions, such as scaffolding and factuality, and study different input configurations that incorporate solution correctness and gold answers. Experiments show that this approach improves both factual accuracy and pedagogical quality over base models and existing tutoring models. Human evaluation further indicates that our best model is competitive with a strong proprietary baseline, while providing additional benefits in terms of openness, transparency, and reproducibility. Our results highlight the effectiveness of preference-based pedagogical alignment, while also revealing challenges in reliably evaluating tutoring quality.
Aligning LLMs for math tutoring typically requires RL-based training with multi-GPU infrastructure. We investigate whether training-free prompt optimization-evolving only the system prompt via API calls-can serve as a practical alternative. We adapt 7 published methods and propose 5 education-specialized methods, evaluating these 12 methods under 5 conditions on 2 OOD benchmark suites. All 12 best-per-method configurations surpass the strongest RL-trained baseline (R_total = 0.633), and our ParetoGrad achieves the best Pareto balance across post-test solve rate, leak control, and helpfulness, rather than dominating any single component. Behavioral analysis with an 82-code educational codebook reveals that training-free methods rely on teaching-knowledge patterns at 2-3x the rate of RL-trained models, with a compensating ~10 percentage-point reduction in intent-level scaffolding. We also find a task-dependent reasoning mode effect consistent across training-free and RL-based paradigms. Our approach enables efficient development of pedagogically aligned LLM tutors with prompts alone and minimal compute.
Novice math teachers often encounter students' mistakes that are difficult to diagnose and remediate. Misconceptions are especially challenging because teachers must explain what went wrong and how to solve them. Although many existing large language model (LLM) platforms can assist in generating instructional feedback, these LLMs loosely connect pedagogical knowledge and student mistakes, which might make the guidance less actionable for teachers. To address this gap, we propose MisEdu-RAG, a dual-hypergraph-based retrieval-augmented generation (RAG) framework that organizes pedagogical knowledge as a concept hypergraph and real student mistake cases as an instance hypergraph. Given a query, MisEdu-RAG performs a two-stage retrieval to gather connected evidence from both layers and generates a response grounded in the retrieved cases and pedagogical principles. We evaluate on \textit{MisstepMath}, a dataset of math mistakes paired with teacher solutions, as a benchmark for misconception-aware retrieval and response generation across topics and error types. Evaluation results on \textit{MisstepMath} show that, compared with baseline models, MisEdu-RAG improves token-F1 by 10.95% and yields up to 15.3% higher five-dimension response quality, with the largest gains on \textit{Diversity} and \textit{Empowerment}. To verify its applicability in practical use, we further conduct a pilot study through a questionnaire survey of 221 teachers and interviews with 6 novices. The findings suggest that MisEdu-RAG provides diagnosis results and concrete teaching moves for high-demand misconception scenarios. Overall, MisEdu-RAG demonstrates strong potential for scalable teacher training and AI-assisted instruction for misconception handling. Our code is available on GitHub: https://github.com/GEMLab-HKU/MisEdu-RAG.
Large language models (LLMs) are increasingly used as AI tutors, but a correct answer is not always a pedagogically appropriate one. In classroom learning, effective help depends not only on correctness, but also on whether a response matches the learner's current foundation, the course sequence, and the timing of concept introduction. Existing evaluations focus mainly on answer quality, leaving this instructional fit under-measured. We present the Pedagogical Suitability Index (PSI), a composite metric of six theory-informed sub-scores that evaluates how well LLM-generated tutoring responses align with learner readiness and curricular progression, and we further use PSI as a structured feedback signal for response improvement. We evaluate four LLM tutors (ChatGPT, Gemini, Gemma4, and Qwen3) across 240 scenario-based evaluations using paired standard and defective prompts, then apply a PSI-guided regeneration protocol to 62 weak-performing cases. Baseline differences across the four tested models were modest overall (PSI range: 0.557 to 0.638), and open-weight and closed models did not exhibit a clear separation in pedagogical fit. Under the tested prompt perturbations, overall PSI remained largely stable (Delta = -0.002), though sub-score trade-offs emerged. More importantly, PSI-guided feedback substantially improved weak-performing cases: 51 of 62 cases improved (82.3%). Focused manual evaluation of the 62 PSI-selected weak cases provides initial evidence that the identified weaknesses are instructionally meaningful and that many PSI-guided regenerations correspond to human-judged improvement. These results suggest that learner- and curriculum-aware alignment may matter more for effective tutoring than model category alone, and that such alignment is both measurable and improvable.