Persistent effects of childhood living arrangements and family change on adolescent outcomes have often been attributed to differences in socialization and intrafamily processes. We use data from the Panel Study of Income Dynamics to assess an alternative explanation: that neighborhood context and residential mobility represent a central set of mechanisms through which family structure affects adolescent risk behavior. Our results indicate that the effects of childhood living arrangements and family change on the risk of dropping out of school (n=8,267) and of experiencing a premarital teen pregnancy (n=6,063) are largely attenuated when differences in the level of neighborhood disadvantage and the number of residential moves experienced by adolescents is taken into account.