This paper examines how homelessness is criminalized in Greensboro, North Carolina, and the ways in which the Homeless Union of Greensboro (HUG) has contested such criminalization. This paper draws on data from a participatory action research study conducted between 2018 and 2020 by a group of researchers from two local universities and members of HUG. Findings from our study suggest that law enforcement officers in Greensboro use a vast array of laws to harass, ticket, and arrest people experiencing homelessness, particularly those who are Black. Findings also suggest that when individuals experiencing homelessness seek help for citations or arrests, it is challenging to access quality, affordable legal representation. This paper illustrates how HUG takes a multi-pronged approach to address the variety of policies and practices that target homeless people, particularly people of color, recognizing that systems change requires a multifaceted approach that adapts to dynamic social and political contexts., (© 2021 Wiley Periodicals LLC.)