Young adults experiencing homelessness (YAEH) have been found to have high rates of prior involvement with foster care and juvenile justice, but little is known about whether YAEH differ in their risk behaviors based on exposure to different systems. This study used a dataset of 1426 YAEH from 7 different US cities to examine the historical risk and resilience characteristics of those involved in foster care alone, juvenile justice alone, both systems (dual status), and no system involvement. Logistic regression was used to examine whether different types of childhood system involvement predicted risk behaviors in young adulthood including substance use, trade sex, suicide attempts, unplanned pregnancy, and involvement in the adult criminal justice system. Notably,57% of youth had been exposed to one of the systems – 20% foster care only (n = 291), 18% juvenile justice only (n = 254), and 18% dual status (n = 261). YAEH without a history of system involvement had significantly lower childhood trauma scores and lower rates of lifetime mental health diagnoses compared to all three system involved groups, with dual status youth having the highest rates of both. In relation to risk outcomes, youth with dual status histories had higher odds of trading sex and those with juvenile justice involvement, either alone or as dual status, had higher odds of being arrested after age 18 and of problematic substance use. Results suggest YAEH with prior involvement in child-serving systems have unique risk characteristics that vary by type of system involvement, with dual-system involved youth at particularly high risk. Findings highlight the need for foster care and juvenile justice systems to work collaboratively in providing preventive interventions prior to system exit.