Recent statistics indicate limited condom use, high STI (sexually transmitted infection) rates, and a general lack of knowledge about reproductive and sexual health among homeless youth. This research focuses on the experiences of homeless female and transgendered youth, providing an insider's perspective on shaping sexual health interventions. This qualitative research is based on life history interviews and participant observation with eight homeless young women who reflect the diversity of the homeless population in Toronto, Ontario, Canada. Their particularized sexual experiences and health-seeking behaviors illustrate the range of issues faced by this community, speaking to the efficacy of current health promotion strategies. Too often faced with judgmental health and social service providers who they perceive to undermine their agency and empowerment, these women highlight the challenges they face when seeking sexual and reproductive health services and information. In addition to speaking to the struggles and frustrations they face in regard to their sexual health and the services with which they choose to interact, the women provide suggestions for improved care. From these, the authors include key recommendations for the provision of culturally competent, sex-positive, and nonjudgmental health services with the hope that health practitioners and promoters can learn from these experiences, both positive and negative, when caring for and supporting young women living in exceptional circumstances.