Youth without housing experience more regulation and conflict with criminal justice than their housed counterparts. Using in-depth qualitative interviews with fifty-one young people, we focus on how efforts to move away from homelessness towards long-term housing stability are impacted by conflict with law, a term referring to a broad range of experiences with various authorities in the legal system, social services, shelters, etc. Our paper comes out of a yearlong longitudinal study of the factors and processes affecting the transition away from youth homelessness in Toronto and Halifax. We consider practical barriers generated by conflict with law, but also the role that it can play in shaping the identity processes at the heart of successful transitions. Our findings highlight how conflict with law and regulation—even occurring before and during homelessness—has serious repercussions for young people well after they have left the streets.