(1) The increase in women’s mass incarceration over the past forty years raises questions about how justice-involved women experience the financial aspects of the criminal justice system. (2) We conducted in-depth interviews with twenty justice-involved women and seven criminal law and reentry professionals, and conducted courtroom observations in southeastern Pennsylvania. (3) The results from this exploratory research reveal that women’s roles as caregivers, their greater health needs, and higher likelihood of being poor creates barriers to paying fines and fees and exacerbates challenges in reentry. (4) These challenges contribute to a cycle of prolonged justice involvement and financial instability.