This qualitative study brings together the voices of parents and their representatives, including attorneys, social workers and parent advocates, to understand the lived experiences of child welfare involved parents as they navigate Family Court, and how to improve it. The findings suggest that these courts are difficult to navigate for both parents and their representatives, and are often experienced as punitive and unsupportive spaces. The findings also reveal a strong congruence between how parents and their advocates wish the courts to operate (and how they sometimes do), and the principles of therapeutic jurisprudence (TJ), which recognizes the emotional and psychological toll legal proceedings can take and suggests ways to minimize that harm. Parents’ relationship with their judge and the judge’s ability to understand and connect with them are identified as transformative factors in the courtroom.