This paper explores the dynamics of caregiver rejection experienced by 40 homeless young adults 19–21 years of age. Using qualitative interviews, our findings reveal that nearly all of the youth reported at least one type of familial rejection that was intertwined with wider household conflict, and several youth experienced multiple types of rejection. Many young people reported “feeling like an outsider,” as they felt marginalized by family members and perceived a sense of outsiderness within their family networks. Some youth cited rejection when they were “betrayed by a primary caregiver for a significant other.” These intimate partners, such as a boyfriend, girlfriend or stepparent, often abused the young person, which exacerbated their experiences with caregiver rejection. Numerous youth were “pushed into institutional living,” such as foster care or group homes, at the behest of their primary caregivers, which stemmed from familial discord and behavioral issues on the part of the young person. In the most explicit form of rejection, youth were “kicked out by a caregiver” and subsequently entered into street life when they had nowhere else to go. Implications of these experiences are discussed, which can impact homeless young people’s future life chances as they attempt to exit the street.