With the emergence of large language models (LLMs) as a powerful class of generative artificial intelligence (AI), their use in tutoring has become increasingly prominent. Prior works on LLM-based tutoring typically learn a single tutor policy and do not capture the diversity of tutoring styles. In real-world tutor–student interactions, pedagogical intent is realized through adaptive instructional strategies, with tutors varying the level of scaffolding, instructional directiveness, feedback, and affective support in response to learners’ needs. These differences can all impact dialogue dynamics and student engagement. In this paper, we explore how tutor personas embedded in human tutor-student dialogues can be used to guide LLM behavior without relying on explicitly prompted instructions. We train a steering vector using preference optimization: an activation-space direction that guides model responses toward specific tutor personas. We find that this steering vector captures tutor-specific variation across dialogue contexts, improving semantic alignment with ground-truth tutor utterances and increasing preference-based evaluations, while largely preserving lexical similarity. Analysis of the learned scaling coefficients further reveals interpretable structure across tutors, corresponding to consistent differences in tutoring behavior. These results demonstrate that activation steering offers an effective and interpretable way for controlling tutor-specific variation in LLMs using signals derived directly from human dialogue data.

Recent advances in large language models (LLMs) have led to the development of AI-powered tutoring systems that provide interactive support via dialogue. To enable these tutoring systems to provide personalized support, it is essential to assess student performance at each turn, motivating knowledge tracing (KT) in dialogue settings. However, existing dialogue-based KT approaches often ignore question difficulty and rely on opaque LLM latent representations, hindering accurate and interpretable prediction. In this work, we propose an interpretable difficulty-aware conversational KT framework that leverages LLMs to explicitly model student knowledge state and the difficulty of tutor-posed tasks at each dialogue turn. The framework incorporates the original question and the next tutor-posed task to estimate the student’s knowledge state and the difficulty of the upcoming turn. It further integrates Item Response Theory to map LLM outputs into student ability and question difficulty parameters, enabling interpretable prediction of student performance grounded in cognitive theories of learning. We evaluate the framework on two tutor-student dialogue datasets. Quantitative and qualitative results show that our framework outperforms existing KT baselines, meanwhile generating interpretable outputs consistent with cognitive theory. Our code and data are available at https://github.com/umass-ml4ed/Difficulty-Aware-DialogKT.

Advances in large language models (LLMs) enable many new innovations in education. However, evaluating the effectiveness of new technology requires real students, which is time-consuming and hard to scale up. Therefore, many recent works on LLM-powered tutoring solutions have used simulated students for both training and evaluation, often via simple prompting. Surprisingly, little work has been done to ensure or even measure the quality of simulated students. In this work, we formally define the student simulation task, propose a set of evaluation metrics that span linguistic, behavioral, and cognitive aspects, and benchmark a wide range of student simulation methods on these metrics. We experiment on a real-world math tutoring dialogue dataset, where both automated and human evaluation results show that prompting strategies for student simulation perform poorly; supervised fine-tuning and preference optimization yield much better but still limited performance, motivating future work on this challenging task.

Vocabulary acquisition poses a significant challenge for second-language (L2) learners, especially when learning typologically distant languages such as English and Korean, where phonological and structural mismatches complicate vocabulary learning. Recently, large language models (LLMs) have been used to generate keyword mnemonics by leveraging similar keywords from a learner’s first language (L1) to aid in acquiring L2 vocabulary. However, most methods still rely on direct IPA-based phonetic matching or employ LLMs without phonological guidance. In this paper, we present PhoniTale, a novel cross-lingual mnemonic generation system that performs IPA-based phonological adaptation and syllable-aware alignment to retrieve L1 keyword sequence and uses LLMs to generate verbal cues. We evaluate PhoniTale through automated metrics and a short-term recall test with human participants, comparing its output to human-written and prior automated mnemonics. Our findings show that PhoniTale consistently outperforms previous automated approaches and achieves quality comparable to human-written mnemonics.

Learning Japanese vocabulary is a challenge for learners from Roman alphabet backgrounds due to script differences. Japanese combines syllabaries like hiragana with kanji, which are logographic characters of Chinese origin. Kanji are also complicated due to their complexity and volume. Keyword mnemonics are a common strategy to aid memorization, often using the compositional structure of kanji to form vivid associations. Despite recent efforts to use large language models (LLMs) to assist learners, existing methods for LLM-based keyword mnemonic generation function as a black box, offering limited interpretability. We propose a generative framework that explicitly models the mnemonic construction process as driven by a set of common rules, and learn them using a novel Expectation-Maximization-type algorithm. Trained on learner-authored mnemonics from an online platform, our method learns latent structures and compositional rules, enabling interpretable and systematic mnemonics generation. Experiments show that our method performs well in the cold-start setting for new learners while providing insight into the mechanisms behind effective mnemonic creation.

Multiple-choice questions (MCQs) are ubiquitous in almost all levels of education since they are easy to administer, grade, and are a reliable format in assessments and practices. One of the most important aspects of MCQs is the distractors, i.e., incorrect options that are designed to target common errors or misconceptions among real students. To date, the task of crafting high-quality distractors largely remains a labor and time-intensive process for teachers and learning content designers, which has limited scalability. In this work, we study the task of automated distractor generation in the domain of math MCQs and explore a wide variety of large language model (LLM)-based approaches, from in-context learning to fine-tuning. We conduct extensive experiments using a real-world math MCQ dataset and find that although LLMs can generate some mathematically valid distractors, they are less adept at anticipating common errors or misconceptions among real students.

In this paper, we study an under-explored area of language and vocabulary learning: keyword mnemonics, a technique for memorizing vocabulary through memorable associations with a target word via a verbal cue. Typically, creating verbal cues requires extensive human effort and is quite time-consuming, necessitating an automated method that is more scalable. We propose a novel overgenerate-and-rank method via prompting large language models (LLMs) to generate verbal cues and then ranking them according to psycholinguistic measures and takeaways from a pilot user study. To assess cue quality, we conduct both an automated evaluation of imageability and coherence, as well as a human evaluation involving English teachers and learners. Results show that LLM-generated mnemonics are comparable to human-generated ones in terms of imageability, coherence, and perceived usefulness, but there remains plenty of room for improvement due to the diversity in background and preference among language learners.