With growing jail populations, more children experience paternal incarceration. Using the life course framework, this dissertation examines how fathers who are transitioning to adulthood navigate parenthood, adulthood, and the criminal justice system. Using an intergenerational approach to understand how identities of fatherhood are constructed and enacted, my dissertation focuses on how fathers in county jails across southern California evaluate (1) their own caregivers as parents, (2) the criteria of a good father and themselves as fathers, and (3) the relationships they have with their children during jail. This project is unique because it draws on 43 semi-structured, open-ended interviews of currently incarcerated young fathers. Findings thus far show congruence with previous research who describe good fathers as people who are accessible to their children, financially provide for them, support them, and guide their children. Fathers prioritize effort from their own caregivers being involved in their lives, offering guidance and working to provide for the fathers. Fathers describe similar importance for good parenting in jail, and by adapting their fatherhood identity, they retain their fatherhood identities while incarcerated. The most advantaged of these fathers, embedded in families able to mobilize to facilitate a father-child relationship experience set-backs in relationships and expect challenges after release. The most disadvantaged, however, become further disconnected from family and alter their fatherhood identity with a nihilistic perspective. Incarceration exacerbates inequalities in families by forcing families to empty resources into jail, an environment that is set up to challenge their ability to stay connected. For those families without these resources, their family connections deteriorate the most.