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Escape from Monkey Island Hints
What should I do in the Pirate Transmogrification Academy?
1 of 3: First, talk to the teacher and tell her you're tired of being a pirate. She'll invite you in to become transmogrified.
2 of 3: The last thing you want would be for Guybrush to get transmogrified. You should avoid this at all costs.
3 of 3: Pick the meanest, most pirate-y thing to say to each of the teacher's questions. She'll lose all hope of converting you and kick you out of the Academy, but you'll get a dunce cap for your efforts.