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Much research indicates that family relationships encourage desistance from crime in adulthood. That research often examines the effects of marriage and parenthood in particular, often revealing beneficial effects on crime even among those with extensive histories of offending. Little is known, however, about whether family variables can similarly encourage desistance during adolescence. At that stage of the life course, family relationships are defined by the family of origin, and the most serious offenders often come from families with troubled or severed relationships and a long history of criminal justice involvement. The exact role that these families may play in promoting favorable shifts among serious juvenile offenders is unknown. This study examines this issue with data from a large cohort of serious offenders released from residential placements in the Florida juvenile justice system. We examine the effects of key family variables on (1) prosocial shifts that youth experience during the residential stay and (2) the odds of recidivism in the 12 months after release. As part of this, we also consider whether effects of family variable are conditional on other factors, including background characteristics of the youth and his or her family.