Since the 1970s, both women’s incarceration and research on incarcerated women have expanded. This qualitative study is unique in reporting perspectives of 37 jail staff members (e.g., supervisors, line staff, and mental and physical health care providers), from four regions of the United States. Interviews explored staff perceptions of women’s pathways to jail and their individual, structural, and reentry needs and challenges, including frequent experiences of interpersonal violence and struggles with mental health. Staff perceptions were consistent with the existing literature. Most of the staff were at least partially sympathetic to and aware of the women’s difficult and varied lives and challenges.