Abstract
LLMs are increasingly used as AI tutors, yet existing benchmarks overlook the challenging behaviors common among students with learning and behavioral difficulties. We introduce TutorCaseBench, a benchmark that grounds AI-tutor evaluation in qualitative case studies from pedagogy, educational psychology, and special education. Our pipeline converts documented student categories into case-specific scenarios, tutor-student dialogues, and rubrics grounded in source evidence. The benchmark contains 923 dialogues across five challenge types, evaluated through open-ended response generation (1,560 items) and multiple-choice selection (2,537 items). Across 11 state-of-the-art LLMs, even the strongest model satisfies a rubric criterion in only 55.8% of open-ended cases, while models are better at selecting appropriate strategies than generating situated responses. These results reveal a gap between intervention recognition and context-specific adaptation, especially for open-weight models. All data are publicly available at this https URL.
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URL
https://arxiv.org/abs/2610.30828
