ABSTRACT The connection between homelessness, social exclusion, and the deprivation of fundamental rights has been extensively studied. The intricate interplay of laws, policies, regulations, institutions, and service practices forms a complex network of mutually reinforcing factors, that can pose a significant challenge to the homeless. This article presents the findings of a qualitative study focused on the Italian nonprofit organisation called ‘Street Lawyers’ (SL) which provides legal assistance and advocacy for homeless people. Due to social exclusion, homeless experience daily violations in exercising their rights and encounter many obstacles within the welfare system. The aim of the research was to investigate how SL's mission is implemented, what needs are met and the complexity of their interventions. The findings demonstrate how, despite the organisation's legal mandate, SL face various difficulties and needs that emphasise the hardships experienced by the homeless people. These issues extend beyond the legal sphere and offer insightful perspectives on the trajectories and support system of the homeless. By revealing the obstacles homeless people face in claiming and enjoying their rights, the article shows the potential of this legal aid practice, particularly when it goes beyond a formal legalistic approach and embraces a socio-political interpretation of rights.