This pilot study was funded by the Canadian Institutes of Health Research and offers an examination of the experiences and perceptions of street youth vis-୶is their health status. Through in-depth interviews and a short quantitative survey with 15 street-involved youth in Halifax, Nova Scotia, this paper explores healthy and not-so healthy practices of young people living on the street. Qualitative interviews with ten health care and social service providers complement the analysis. More specifically, the investigation uncovered how street youth understand health and wellness, how they define good and bad health, and their experiences in accessing diverse health services.