The recent Supreme Court decision in Mahanoy Area School District v. B.L. ex rel. Levy expanded the authority of school leaders to censor student off-campus online speech under certain circumstances. However, the Court failed to articulate the contexts in which censorship is constitutionally permissible. The absence of a clear constitutional standard leaves school leaders with unbridled discretion to censor off-campus speech, thereby increasing the likelihood of viewpoint discrimination. The expansion of school leaders’ authority to censor student speech is occurring during a renaissance of political and social activism in K-12 schools as students, especially those from marginalized populations, advocate for myriad controversial issues affecting their communities such as gun control, reproductive rights, and LGBTQI+ rights. This is occurring during a broader backlash against progressive political speech: anti-CRT; “Don’t Say Gay”; and the weaponization of the “woke” trope to suppress speech and maintain the subordination of marginalized groups. This Essay offers a path toward safeguarding students’ First Amendment rights to engage in online expressive activities, political speech, and symbolic speech off campus through the adoption of a new constitutional standard, the Integrated Contextual Disruption (ICD) Test. This proposed new standard strikes the necessary balance between a school’s regulatory interest in maintaining an environment conducive to learning and the competing value of student free-speech rights.