The Article focuses on the impact of US sanctions on protected speech and association. The core argument is that US sanctions—directly and indirectly—restrict speech that should be protected by both the Constitution and statute, and chill a great deal more protected speech. The chilling effect of the economic sanctions administered by the US Treasury Department has been amplified by the categories of speech that are prohibited by the material support statute. I argue that neither OFAC’s enforcement discretion nor its licensing policy are adequate safety valves when it comes to securing constitutionally protected speech. Rather, important, but relatively low cost, reforms are needed, both to the material support statute and OFAC’s regulations and licensing process. The material support statute should be amended to include a requirement of specific intent to further the unlawful aims of a proscribed organization before criminal liability attaches. OFAC’s regulations should be amended to include explicit references to the Berman Amendment across all of its sanctions regimes, with clear examples of speech activities, such as organizing political dialogue or peace negotiations, that do not qualify as prohibited “services” even when they involve designated individuals or entities. Finally, OFAC’s licensing process should be reformed to fast-track requests for interpretive guidance and specific licenses when constitutionally protected speech and association is at stake.