This report is an examination of a theoretical model of risk amplification within a sample of 255 homeless and runaway adolescents. The young people were interviewed on the streets and in shelters in urban centers of four Midwestern states. Separate models were examined for males (n = 102) and females (n = 153). Results indicated that street experiences such as affiliation with deviant peers, deviant subsistence strategies, risky sexual behaviors, and drug and/or alcohol use amplified the effects of early family abuse on victimization and depressive symptoms for young women. These street adaptations significantly increased the likelihood of serious victimization over and above the effects of early family history for both young men and women. Similarly, street behaviors and experiences increased the likelihood of depressive symptoms for young women over the effects of early family abuse, but not for young men. The risk-amplification model from the life course theoretical perspective is discussed as an example of the cumulative continuity of maladaptive behaviors.