Homelessness is punishing to those who experience it, not just from the inherent and protracted trauma of living exposed on the street, but also due to widespread and pervasive laws that punish people for being homeless. People experiencing homelessness, particularly chronic homelessness, often lack reasonable alternatives to living in public. Yet cities throughout the country are increasingly enacting and enforcing laws that punish the conduct of necessary, life-sustaining activities in public, even when many people have no other option. These laws are frequently challenged in court and often struck down as unconstitutional. But legally sound, cost-effective, and non-punitive alternatives to ending chronic homelessness exist. This article exposes some of the problems with criminalization laws, not only for people experiencing homelessness, but also for the broader community. It discusses how current approaches often make chronic homelessness worse and explains why non-punitive alternatives, especially Housing First and permanent supportive housing, are the most cost-effective means of addressing chronic homelessness. Ultimately, this article urges cities and their constituents to stop punishing homelessness and instead to start solving it.