As winter bares down on some of the larger metropolitan areas, this article explores the morality of some of the laws that leave the homeless stranded in crippling temperatures. At the center of the debate is the law imposed by many cities banning “urban camping” and recent videos that have surfaced showing police issuing citations to residents of an encampment in Denver. This brings to light the “civic soul-searching” that cities must partake in as activists continue to push for the right to rest as a civil right for the homeless. Portland saw its progressive homeless law that allowed tent camping and sidewalk sleeping revoked this month after a sea of complaints flooded the mayor’s office. Though initially unsuccessful, Portland represents a progressive city attempting to address homelessness and its policies would surely be deemed more successful if there were designed spaces integrated into the landscape that could serve as a public space and a refuge for area homeless. If this were the case, would right to rest and urban camping be seamlessly and effectively added to the urban fabric.