Our presentation reports on data from a project focused on the trajectories of young people experiencing homelessness and housing precarity in 4 Canadian cities (n=80). Following participants for up to two and a half years, we combined quantitative survey and qualitative interviews to better understand how young people experience and navigate transitions towards stability. Here, we focus on conflict with law (criminal, immigration, family, housing) as well as conflict with other authorities, and consider how these experiences intersect with housing-related trajectories. We report on issues and experiences youth related to us about police, courts, and corrections – but also to child/youth protection and case managers or security guards at school or in shelters. Our analysis shows how these experiences can be impactful - and harmful – shaping both self-concept, and chances at accessing success and stability. Our findings highlight the importance of opposing punitive and exclusionary practices, and identifies some promising practices that can support youth.