This Article focuses on two areas of national security exceptionalism in free speech doctrine: judicial review of material-support laws as applied to speech and judicial responses to free speech defenses to prosecutions for leaking classified information. While there are important differences between these two areas, they share one significant feature. In both realms, courts engage in a very particular kind of “national security bootstrapping.” Specifically, courts effectively treat administrative designations—the decision to label a group a terrorist organization in one case and the decision to classify information in another—as means to bypass the rigorous judicial review to which related speech restrictions would otherwise be subjected.

With respect to material-support laws, the U.S. Supreme Court has shown extraordinary deference to such laws as applied to speech “coordinated” with a designated “foreign terrorist organization” (FTO). Were it not for the terrorist designation, courts would view such restrictions with the utmost skepticism. With respect to classified information, courts have, in the handful of cases on the topic, reviewed prosecutions for leaking classified information with dramatically less rigor than they review restrictions on unclassified statements that the government deems dangerous.

It is troubling that courts treat administrative designations—specifically, both FTO determinations and information classification—as bootstraps by which to yank speech restrictions from the clutches of probing judicial scrutiny. This Article builds on existing scholarly critiques to identify and examine the common thread of national security bootstrapping that runs through both sets of cases. The hope is that in so doing, some greater light may be shed both on the cases themselves and, more broadly, on the costs and benefits of judicial deference to executive national security claims where civil rights and civil liberties are at stake.