Swedish social services rest on strong institutional legitimacy, yet levels of trust in the organization and its professionals vary across different groups. Outreach social work targeting young people aims, in the spirit of prevention, to actively seek out and engage those who would not otherwise encounter social services –”the hard to reach”. While previous research has largely examined how low trust affects service users and those under investigation, far less attention has been paid to legitimacy–an issue that is crucial in outreach work, where social workers initiate contact. Because young people may view such approaches as intrusive or illegitimate, outreach workers must negotiate situational legitimacy to gain recognition and acceptance. This study draws on participant observations and interviews with outreach workers, young people, and unit managers to analyse the conditions that shape these legitimacy-building processes and how they are managed in practice. The findings show that outreach workers navigate multiple audiences: a primary audience–the youth themselves–and a secondary audience consisting of collaboration partners, policymakers, and other actors present in public settings. Another finding highlights how outreach workers negotiate contextually, shaped by time and place, seeking acceptance that grants them the mandate to pursue broader preventive goal, a process conceptualized in terms of situational legitimacy.