In The Headmaster: Debbie's Halloween, you guide Debbie as she takes charge while the staff enjoys their party. It's her job to ensure all the girls return to their dorms by curfew. If she succeeds, she'll be allowed to join the party and might even get a chance to impress her crush, Miss Newman. But if she fails to gather all the girls by curfew, she'll face a spanking from the headmaster.