This paper illuminates the street-level experiences of harm reduction workers in San Francisco and their strategies for building trust with people who inject drugs (PWID), a heavily stigmatized population. Existing literature addresses topics like stigma, substance use, and outreach work; however, few studies focus on the harm reduction workforce, and those that do often originate from international settings where harm reduction is more prevalent. In this paper, through 15 semi-structured interviews with outreach workers and health professionals, I find that respondents face political resistance, police tensions, and burnout. To navigate these barriers, workers utilize strategies like lived experience, signaling, and community-based care. Based on these findings, I argue that policymakers should legalize harm reduction practices like supervised injection sites (SIS), allocate funding towards outreach organizations, and implement initiatives to destigmatize substance use. The findings presented here give insight into the harm reduction workforce and the vulnerable populations they serve.