Recent studies of the transition to adulthood advocate taking a person-centered approach and modeling key transitional events simultaneously. This article advances this literature by focusing on precarious transitioning among at-risk youth and relating their transition experiences to criminal offending. I find evidence for three distinct "pathways" to adulthood. Those with juvenile convictions are equally likely to take one of two "precarious" routes to adulthood—an early family starter pathway or a stalled pathway. Importantly, early family starters are much less likely than stalled transitioners to offend as adults. The findings suggest the transition to adulthood represents a fork in the road for juvenile delinquents in which early family starting serves as an avenue out of continued offending.