Youth who identify as lesbian, gay, bisexual, transgender, or questioning (LGBTQ) are over-represented in the child welfare system and also among people experiencing homelessness. This article reports on the experiences of youth who identify as LGBTQ and also have previous child welfare system involvement-as compared to youth identifying as heterosexual, cisgender-as a subsample of youth experiencing homelessness in a southeastern metropolitan area. The study sample was comprised of primarily black males who reported an average age of 21. Approximately one third of youth identified as LGBTQ. Over half of the youth in the sample had been in foster care, while 43% indicated some other form of child welfare system involvement. Of those who had been in the foster care system, 11% were eligible to return to care based on their age. When compared to their heterosexual, cisgender counterparts, a greater percentage of youth who are LGBTQ had been kicked out of their homes, had been homeless for more than one year, reported being abused as a child, were victimized while they were homeless, indicated a mental health problem, and identified adult friends or a professional contact (rather than family members) as a source of support. Fully 95% of both groups in the sample reported some form of trauma. Findings support the need for child welfare system workers to adopt identity affirming, trauma-informed practices with youth who are in care and highlight the challenges in preparing youth for successful, independent living. The child welfare system and homeless providers should deliver a coordinated response to both prevent pathways to system involvement and intervene when necessary.