To what extent should a person be able to contractually bind himself to keeping quiet? Should such promises be as readily enforceable as promises to sell cotton or paint a house? Or do they raise First Amendment or public policy concerns that warrant greater regulation? On the one hand, promises to keep quiet are routinely used by businesses to protect trade secrets and other types of proprietary information. Individuals also rely on confidentiality promises when they provide sensitive financial or medical information to service providers. On the other hand, promises to keep quiet are sometimes used to suppress speech about criminal or tortious conduct, or speech about embarrassing but important information. In this article, I explore whether these and other types of contracts of silence should be enforceable. My thesis is that contracts of silence threaten public access to information and, therefore, warrant careful judicial regulation. While recognizing that parties may voluntarily enter into contracts of silence, and that parties may receive separate compensation for their commitments to silence, I nevertheless recommend that courts deny enforcement to contracts when the public interest in access to the suppressed information outweighs any legitimate interest in contract enforcement.