Commentators have leveled trenchant critiques of collateral consequences of criminal conviction, analogizing them to a form of “civil death.” This Essay develops the related concept of “civil death by a thousand cuts” in two senses. First, penalties such as voting bans or deportation after a conviction are often just the tip of the iceberg. Second, a system of far-flung, intertwined civil and criminal penalties portends the death of a civil society capable of recognizing and mediating excessive penalties. Recognizing how these penalties operate—and how difficult they can be to address—is a critical step toward creating a more proportionate criminal legal system.