Edustories: A Collection of Real-world Case Studies from Classroom Practices

Educational NLP systems are typically evaluated using engagement metrics and satisfaction surveys, which are at best a proxy for meeting pedagogical goals. We introduce six computational metrics for automated evaluation of pedagogical alignment in student-AI dialogue. We validate our metrics through analysis of 12,650 messages across 500 conversations from four courses. Using our metrics, we identify a fundamental misalignment: educators design conversational tutors for sustained learning dialogue, but students mainly use them for answer-extraction. Deployment context is the strongest predictor of usage patterns, outweighing student preference or system design: when AI tools are optional, usage concentrates around deadlines; when integrated into course structure, students ask for solutions to verbatim assignment questions. Whole-dialogue evaluation misses these turn-by-turn patterns. Our metrics will enable researchers building educational dialogue systems to measure whether they are achieving their pedagogical goals.

Chatbots have long been explored as tools to support learning, and recent advances in large language models have significantly expanded the availability of platforms for educators to author AI tutoring chatbots. Yet effective authorship demands more than writing a system prompt; it requires educators to act as learning designers, AI interaction designers, and QA engineers. In practice, however, teachers rarely fulfill these roles. Our formative study found that virtually none systematically tested their bots before deploying them to students. To address this gap, we present PromptDecipher, a system that restructures the authoring workflow around a direct correction-based interaction rather than writing abstract system prompts, teachers interact with a live chat preview and edit undesirable bot responses. An automated pipeline then analyzes the correction, proposes a targeted system prompt rewrite, and validates the change across pre-defined test scenarios. This enforces QA as a first-class activity and scaffolds teachers in roles they would otherwise skip. PromptDecipher will be deployed in an AI for Educators course enrolling hundreds of higher-education instructors. A live prototype (https://teacher-prompting.vercel.app/), an anonymized codebase (https://anonymous.4open.science/r/teacher-prompting-2EDF/), and anonymized demo (https://tinyurl.com/las-prompt-decipher-demo) are available via links in the footnote.

This work introduces AIriskEval-edu-db2, a new dataset designed to train and evaluate auditors based on LLMs for an explainable pedagogical risk assessment in instructional content for grades K-12. The dataset comprises 1,639 explanations from 170 curated ScienceQA questions, covering science, language arts, and social sciences. For each question, the dataset includes an explanation written by a human teacher alongside 11 explanations generated by LLM-simulated teacher profiles associated with distinct pedagogical risks. We propose a comprehensive risk rubric aligned with established educational standards that covers five complementary dimensions: factual precision, depth and completeness, focus and relevance, student-level appropriateness, and ideological bias. A key contribution is the addition of 785 explanations with structured explainability annotations, including risk localization and risk description. The annotations are produced through a semi-automatic process with expert teacher validation. Finally, we present validation experiments comparing state-of-the-art proprietary models with a lightweight local Llama 3.1 8B model in both the pedagogical risk detection and the explainability assessment. These experiments evaluate whether supervised fine-tuning on AIriskEval-edu-db2 enables a locally deployable model to approach or outperform stronger frontier models while preserving privacy in educational auditing and assessment tasks.