This Note examines the current doctrinal difficulties with student Internet speech. Student speech was traditionally protected from school authority when it was performed off campus—it received full First Amendment protection as opposed to the lower level of protection that on-campus speech received. However, the emergence of the Internet as a dominant form of communication has complicated this framework by blurring the line between off-campus and on-campus. As reflected in the Supreme Court jurisprudence, the question of the standard of protection to apply highlights the educational and constitutional issues at stake in student speech. While some courts seem willing to subject all youth speech to the lower constitutional standard, I propose a more nuanced approach. My approach, which I dub the “relational approach,” reframes the debate by reference to the role schools play in our society. The relational approach forces judges to examine the context in which the speech takes place and determine whether society expects such context to be governed by institutional educational authority. By adopting my approach, a more honest and reasonable jurisprudence can emerge.