Family science and public health scholars have documented the consequences of incarceration for the well-being of individuals, children, families, and communities. Yet the largest form of supervision in the criminal legal system is not imprisonment, but probation, with little known about the experiences of parents on probation. We analyzed interviews with 153 adults on probation, 68 (44%) of whom reported being parents of minor children (under 18 years). Compared to participants without minor children, parents with minor children were younger and more likely to be employed. Among parents, 42% reported having custody of one or more minor children and 20% lived with their minor children at the time of the interview. Yet, most (82%) parents reported they provided some form of care or support. Qualitative analyses of four case studies show the challenges facing parents on probation and the complex intersection of custody, living arrangements, and care and support for minor children. We find that parenthood and probation are interconnected, with parent status influencing the experience of supervision and probation impacting parenting opportunities and constraints. Findings suggest service providers working with parents on probation need to attend to these complex family dynamics.