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While rates of youth homelessness appear to be increasing across different countries, young people experiencing homelessness face particularly critical situations, with a notably high prevalence of mental health problems and extended histories of stressful life events. This article analyzes the life trajectories and current health and needs of 392 individuals experiencing homelessness (207 men and 185 women) in the city of Madrid (Spain). People who had first experienced homelessness during their youth (under the age of 30) were, on average, younger but had experienced longer and more frequent episodes of homelessness. They had also been exposed to multiple stressful life events early in life and had a higher prevalence of victimization and criminal justice involvement throughout their lives. Likewise, youth-onset homelessness was associated with lower use of healthcare services, increased rates of mental health diagnoses and suicide attempts, and more symptoms of anxiety, depression, and substance dependence. The ongoing adversity experienced by individuals who experienced youth-onset homelessness suggests that social support systems may be failing to address the needs of vulnerable families and children. These deficiencies may contribute to the intergenerational transmission of poverty and disadvantage, and lead to situations of greater hardship for people experiencing youth-onset homelessness.