As principal of the School of the Arts in San Francisco, Donn Harris is passionate about protecting his students' experiments in free expression. But about two years ago he encountered an example of creative student speech he couldn't support--a nasty post on the MySpace.com Web site that targeted some of the school's students. Deciding that his devotion to free speech had to take a back seat to his responsibility as a school administrator, Harris promptly suspended the responsible student and asked that the page be pulled off the Web. He called a school assembly to discuss the offensive MySpace page and asked students who had signed on as "friends" of the site to apologize for the cruel statements they had endorsed. This article describes how Harris' dilemma is becoming increasingly common among schools across the country. Ideas on how educators can protect inexperienced social networkers are presented.