In Winnipeg, community-based youth serving agencies have raised serious concerns about young people who are becoming homeless due to numerous systems-based issues that are beyond the control of the youth themselves and th e agencies supporting them. Researchers and policy experts across Canada have stated that to prevent and end youth homelessness, there is a need to understand the “systems” that lead youth into and out of homelessness. The University of Winnipeg (U of W), The Social Planning Council of Winnipeg (SPCW) and Resource Assistance for Youth (RaY) partnered to conduct a research study to explore the systemic factors contributing to youth living on the street or in various types of insecure shelter for prolonged periods of time. Youth who have experienced homelessness were interviewed to develop timelines of their lives, identifying the government systems interactions they had. A majority of the youth (18 of 22) were involved with Child and Family Services, and instability and inadequate transitions from care and preparation for adulthood were said to be directly related to their later homelessness. Additional systemic barriers to sustainable income and housing were identified by the youth in their interactions with Justice, Employment and Income Assistance, and Health, Mental Health and Addictions Services. Interviews were then held with government employees and staff of community-based youth serving organizations. Government systems serving youth who are homeless were analysed and case studies for each of them were developed. The research team identified specific policies and program gaps in government systems to be addressed if we wish to prevent or reduce youth homelessness in Winnipeg.