Background: The role that fathers play in the lives of their families, particularly, the lives of children, is vitally important. Research has found positive associations between father involvement and factors, such as infant cognitive outcomes, children’s school-readiness where levels of mothers’ supportiveness are low, better socioemotional, and academic functioning in children. Black males, many who are fathers, are disproportionately overrepresented within the criminal justice system. High incarceration rates have significant economic and social impacts on families and communities. Objective: This article examines differences in father involvement among Black fathers with criminal records and explores relationships between fathers’ involvement, the amount of time served in jail, fathers’ employment status, and fathers’ education levels. Method: Secondary analysis of the third wave of Fragile Families and Child Wellbeing (FFCW) public-use dataset was used for this article. The FFCW study follows a panel or cohort of 4,700 children born to unwed (3,600) and married (1,100) parents. The Fragile Families study employed a stratified random sample of 75 hospitals across 20 U.S. cities with populations over 200,000. Findings: The results of the analyses found (a) that the time served in jail had no effect on fathers’ involvement, (b) no statistically significant differences in fathers’ involvement based on fathers’ education level, and (c) fathers who were working were more engaged in the lives of their children, as compared to fathers who were not working and under correctional supervision. Conclusion: This article’s exploration of differences and relationships between father involvement and socioeconomic variables among Black fathers with criminal records further demystifies the complexities of fragile family compositions and circumstances while informing future policy, practices, and research.