Build and Break Your School’s AI Tutor: One Hour to Write the Rules, Test Them and See Which Ones Hold

Many schools are giving students an AI tutor, or are about to. Few have written down what that tutor is allowed to do, and fewer have tried to make it misbehave before students do.

In this hands-on workshop, small groups design a tutor for a real audience they choose (a subject, an age group, a specific task such as revising for a test or getting feedback on a draft). In fifteen minutes they write its rules in plain language: what it does, what it refuses, how it answers a student who just wants the homework done, how it handles sources and mistakes.

They set it up as a Project or custom assistant in whatever tool their school already uses; no specific product is required or promoted.

Then the groups swap tutors and try to break them: get the solution without doing the work, make the tutor invent a quotation, push it out of its role, make it grade unfairly. Each break is logged.

We close by comparing which rules held and which collapsed, and by rewriting the failed ones together. The exercises come from three years of running the same build-and-break routine with adult learners in Italy, from teachers to company staff: the rules that fail are almost always the same, and they are the ones nobody thought to write.

Key Takeaways

Participants leave with:

• Their tutor’s rule sheet
• A red-team checklist to run with students and colleagues
• A simple habit: never deploy an AI to students you have not tried to break first