Prior research has yet to address how criminal legal system actors take parenthood into account when imposing and enforcing LFOs. Drawing on evidence from 205 semi-structured interviews conducted across four states, this study explores the relationship between monetary punishment and parenthood from the perspectives of court and community corrections professionals. Engaging Kathleen Daly’s framework of familial paternalism (1987a, 1987b, 1989a, 1989b), we find that system actors obtain and interpret information about defendant circumstances to (1) consider family complexity, (2) construct deservingness and (3) curb spill-over punishment. Ultimately, we find that system actors consider parental status in relation to LFOs and defendants’ ability to pay, though their decisions also hinge on gender and the nature of parental involvement.