TutorCaseBench: A Case-Grounded Benchmark for Evaluating LLM Tutors in Supporting Students with Challenging Behaviors

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 https://github.com/kixlab/TutorCaseBench.