Mental health professionals and researchers have emphasized the importance of conducting outreach to locate homeless persons with mental illness, and of creatively engaging these persons into a therapeutic relationship. These outreach and engagement activities raise challenging issues in the areas of client-staff boundaries, professional ethics, and staff safety. While several issues in each of these three key areas have received attention in the growing literature on homelessness, certain issues within each area remain unexplored. The authors draw from the street experiences of outreach staff in a federally funded homeless outreach project to further explore each of these areas, and suggest that experiences of outreach workers are essential in shaping and redefining work activities in these, and other important areas.