This Comment suggests that the debate surrounding the constitutionality of regulations of high school speech needs to be reframed. It observes that the advent of the Internet has fundamentally changed the way individuals communicate. This Comment then discusses the unique problem the Internet has presented for courts attempting to discern under what circumstances schools can restrict students’ off-campus Internet speech without running afoul of the First Amendment. Under the current law, courts employ a test that weighs the interests of the school against the interests of the student to determine whether regulation of speech is permissible. This Comment suggests that this balancing test favors schools’ interests over students’. Therefore, like the Supreme Court has done in many instances, this Comment looks to psychological research to help even out the scales in this arena. Psychological research shows that adolescents have diminished decision-making capabilities. This Comment argues that this reality must be considered when courts are determining whether schools can permissibly regulate student speech. It accordingly suggests two specific changes to the current standard to ensure that the law appropriately reflects reality.