Recent examinations of prisoner reentry for youth typically ignore both the lived experience of incarceration and the cultural milieu to which young people must return. Here, I examine incarceration and community reentry for a prospective, longitudinal sample of 15 young, black and Latino men returning to Philadelphia. I employ participant observation and in-depth interviews with the study participants for approximately three years, to answer the following: (1) How do they experience and interpret youthful incarceration? (2) How do they navigate the "dual transition" from facility to community and from adolescence into young adulthood? and (3) How do they approach the issue of personal change and with what apparent consequences? The case studies detailed here offer insight into the relationships between youth reentry, transitions to adulthood, and further offending for young men of color. Among this group, the transitions most frequently identified by scholars as facilitating desistance, or termination of criminal careers---marriage, fatherhood, and steady employment---are less likely to occur. I describe their attempts to establish households with the mothers of their children and argue that their marginal role in the labor market ultimately results in their failure to meet their own and their partners' expectations for being a good father. I also illustrate a number of structural and cultural barriers to steady legal employment, including the increased use of pre-employment screening techniques and blurred moral and legal boundaries between the formal and informal economies. These family and labor market forces converge to increase the attractiveness of the underground economy, both as a means of regaining a lost sense of respect and for buying a financial stake in the household. Finally, I argue that young men of color experience incarceration as a cultural assault, eroding the institution's legitimacy and ability to effect meaningful change. Because reform schools fail to acknowledge the structural sources of offending, ignore the importance of cultural identity, and offer little in the way of sustained support upon return to the community, they miss important opportunities for strengthening young men's positions in the family and labor market and fail to alter their criminal trajectories.