Threats of violence, even when not actually carried out, can inflict real damage. As such, state and federal laws criminalize threats in a wide range of circumstances. But threats are also speech, and free speech is broadly protected by the First Amendment. The criminalization of threats is nonetheless possible because of Supreme Court precedents denying First Amendment protection to “true threats.” Yet a crucial question remains unanswered: What counts as a true threat?

This Note examines courts’ attempts to answer this question and identifies the many ambiguities that have resulted from those attempts. In particular, this piece highlights three frontiers of judicial confusion that are likely to arise in a true threat case: (1) what type of intent the First Amendment requires, (2) the proper standard of review on appeals of true threat convictions, and (3) the contextual analyses in which courts engage to assess whether a threat is “true” (and, by extension, whether a threat conviction was constitutional). This third frontier is discussed most extensively, as it has the greatest impact on a case’s ultimate outcome. This Note also proposes a new framework for inquiries into the context of true threats, adapted from defamation law, in order to increase consistency and ensure adequate protection of speech rights within the chaotic true threat doctrine.