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In response to the increasing presence of vulnerable individuals in transit systems during the COVID-19 pandemic, Philadelphia’s Project SCOPE deployed outreach teams to connect individuals experiencing homelessness, addiction, and mental health crises with social services while reducing police interventions. This study examines the role of outreach workers with lived experience—often including substance use and homelessness (n=16)—from two Philadelphia-based agencies. Through in-depth interviews, we explored how their personal histories inform their professional practice in transit settings. Findings indicate that lived experience enhances outreach workers’ ability to build trust and form meaningful connections with vulnerable individuals, positioning them as credible sources of support and recovery. Their familiarity with high-risk environments also fosters resilience in managing threats and conflict—challenges that professionals without similar backgrounds may struggle to navigate. Contrary to concerns about relapse risk, exposure to active drug use did not undermine workers’ stability; rather, their firsthand knowledge of these settings became an operational asset. This study contributes to the literature on peer support within justice-adjacent interventions, offering insights for transit authorities and law enforcement agencies seeking to develop outreach models that leverage lived experience as a key component of effective service delivery.