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Using intensive qualitative interviews with 40 homeless youth, this study examined their early family histories for abuse, neglect, and other family problems and the number and types of transitions that youth experienced. Multiple forms of child maltreatment, family alcoholism, drug use, and criminal activity characterized early family histories of many youth. Leaving home because of either running away or being removed by child protective services often resulted in multiple transitions, which regularly included moving from foster care homes to a group home, back to their parents, and then again returning to the streets. Although having experienced family disorganization set youth on trajectories for early independence, there were many unique paths that youth traveled prior to ending up on the streets.