Most of us teach Microsoft AI features long before we see what happens to them in a real tenant. I have spent the last eighteen months on both sides of that gap: delivering the courses, and running the actual Copilot and Microsoft 365 rollout for a 150-user manufacturing group, from Entra ID and conditional access through Purview-based data governance to the adoption budget I had to defend in front of a board. This session is the field report. Which prerequisites silently break the demo. What the labs do not prepare learners for. Where governance stops being a slide and becomes the reason a project is paused for a quarter. Why the questions that sink an AI rollout are almost never the ones asked in the classroom. I will walk through what went wrong, what I would sequence differently, and the specific changes I have made to my own courses as a result. You will leave with a short list of things worth adding to your delivery, and a clearer sense of the questions your learners will face from their own management three months after your course ends.