This analysis draws on longitudinal, qualitative interviews with disadvantaged mothers and fathers who participated in the Fragile Families Study (a U.S. birth cohort study) to examine how issues related to men’s employment, social support, skills, and motivation facilitated their care of young children in different relationship contexts. Interviews with parents indicate that while some motivated and skilled men actively chose to become caregivers with the support of mothers, others developed new motivations, skills, and parenting supports in response to situations in which they were out of work or the mother was experiencing challenges. These findings suggest that disadvantaged men who assume caregiving responsibilities take different paths to involvement in the early years after their child’s birth. Policies that overlook paternal caregivers may not only miss the opportunity to support relationships that benefit at-risk children but also unintentionally undermine this involvement.