EduWild: How Teacher-Configured Chatbots Fail in Real-World Use and How to Fix Them

Abstract

Teachers increasingly configure educational chatbots through natural-language instructions, but how these bots fail in real-world use remains poorly understood. We introduce EduWild, a dataset of 1,726 conversations with 217 teacher-configured chatbots, each paired with the instructions and configuration behind it, including 900 conversations from the intended end users of 35 deployed chatbots. We develop a 29-code taxonomy covering factual, workflow, diagnostic, and pedagogical failures and apply it using a human-calibrated LLM judge. The most frequent failures are lapses in following teacher intent --- bots skip required workflow steps (53.8% of end-user conversations), omit expectation setup (33.4%), and overload learners with information or questions (37.1%). Guided by these findings, we design a prompt-based harness targeting the six most frequent failure modes. In a study with 200 college students across ten bots, the harness reduces the mean number of target failure codes per conversation from 1.406 to 0.489, a 65.2% relative reduction with bots weighted equally. These findings show how real-world failure analysis can guide practical improvements to educational chatbots.