Service access and acquisition are often complex and sometimes dangerous for transgender and gender expansive young people, who frequently experience stigma and discrimination and face systemic barriers including sex segregated programs and institutional practices that deny their own understanding and articulation of their gender. A common theme in the literature is recognition of the need for affirming services specifically designed to meet the needs of transgender young people experiencing homelessness, as this population may not utilize or have access to much needed services due to systemic barriers and fear of rejection and harassment. The current study investigates the lived experiences of transgender and gender expansive young people with histories of homelessness. This phenomenological qualitative investigation explores aspects of transgender and gender expansive youth's experiences, both at home and on the street. A recurring theme emerged in the participants' narratives — the seemingly insurmountable barriers constructed by systems that were not designed with their unique needs in mind. When understood through the lens of cisgenderism, the findings illuminate the structural barriers that exist for transgender and gender expansive young people and the systemic challenges service providers must address.