People who use drugs (PWUD) commonly experience housing instability due to intersecting structural vulnerabilities (e.g., drug prohibition, discriminatory housing policies), and prejudicial or illegal evictions are common. In Vancouver, Canada, evictions have proliferated in the Downtown Eastside, a historically low-income neighbourhood with high rates of drug use and housing instability, resulting in many PWUD being evicted into homelessness. This study characterizes housing trajectories of recently-evicted PWUD through the lens of the institutional circuit of homelessness, and explores how wider contexts of structural vulnerability shape experiences within this. Qualitative interviews were conducted with PWUD recently evicted in the Downtown Eastside (<60 days). Peer research assistants recruited 58 PWUD through outreach activities. All PWUD participated in baseline interviews on the causes and contexts of evictions. Follow-up interviews were completed with 41 participants 3–6 months later, focusing on longer-term impacts of eviction, including housing trajectories. Most participants were evicted into homelessness, remaining so at follow-up. Participants described patterns of residential instability consisting of frequent cycling between shelters, streets, and kin-based networks. While participants normalized this cycling as characteristic of their marginalized social positions, narratives revealed how the demands of the institutional circuit deepened vulnerabilities and prolonged experiences of homelessness. Experiences were framed by participants' (in)ability to navigate survival needs (e.g., shelter, drug use), with tensions and trade-offs between needs increasing participants' and their peers' risks of harms. Constructions of agency further shaped experiences; accounts highlighted tensions between the control inherent to indoor spaces and participants’ need for autonomy. Findings demonstrate how the demands of the institutional circuit foregrounded structural vulnerabilities to perpetuate cycles of instability. Interventions that address survival needs and preserve agency will be necessary to mitigate risks within the institutional circuit, in tandem with upstream interventions that target housing vulnerability and broader social-structural conditions (e.g., poverty, affordability) that entrap recently-evicted PWUD in the institutional circuit.