Middle school is a time in children's lives when they experience tremendous changes: physically, emotionally, and socially. It is a very vulnerable stage when children are exposed to risky behaviors, intense peer pressure, and a possible academic decline. Parents need to be aware of the issues and challenges that their children face so that they can help to solve problems in a proactive manner. When parents work closely with school personnel, young adolescents are guided more effectively. The author, who has worked as a middle school counselor, reveals actual problems that a school counselor might encounter among students and provides vignettes of student situations and conversations with parents. She provides many suggestions to help parents establish boundaries for their children and give guidance as they navigate the troubled waters of early adolescence. She stresses that parents who are informed about the problems their children will face can better help them deal with the issues.