This article argues that we should rethink homeless people’s punishments for violating quality-of-life ordinances. Those ordinances prohibit acts that are deemed to constitute urban nuisances—urban camping, public urination, and sleeping on sidewalks among them. Violating quality-of-life ordinances can result in expensive fines, administrative fees, and civil consequences for unpaid fines. In line with other scholars’ work, this article demonstrates how our current punishment scheme entrenches individuals in homelessness and operates like a self-fulfilling prophecy. Lacking a private property right and stuck in a cycle of homelessness, homeless people will continue to alleviate their needs on public property and be subject to further coercion and punishment. Homeless people’s punishments for violating quality-of-life offenses are also objectionable because they violate three types of proportionality constraints: the gravity of the prohibited conduct, the homeless person’s moral blameworthiness, and their personal situation. This article proposes an alternate punishment scheme that minimizes the prospect of entrenchment in homelessness and remedies those three proportionality concerns. It argues that the state should adopt a day-fine model for financial penalties, implement criminal justice debt absolution frameworks, and rethink the civil and criminal consequences associated with unpaid fines. A more proportional punishment scheme is neither a solution to the reality of homelessness nor a substitute for the state’s responsibility to ensure better access to housing. However, this article’s proposals can mitigate the gravest consequences associated with homeless people’s punishments, prevent entrenchment in homelessness, and ensure homeless people are treated with greater respect.