This paper brings a close analysis to bear on tensions in the main discourses within probation and the wider criminal justice system, namely between punitive, target-driven approaches and the opposing gender-responsive, strengths-based, humanitarian, individualised ones. Drawing on a pilot study, which is an early part of the author's Ph.D., the article explores how probation practitioners attempt to work constructively within the constraints of statutory supervision and how the pressures and dilemmas are managed. Qualitative research methods were used whereby data were collected through videoing the supervision sessions of probation officers and women service users, as well as participant observation at probation meetings and in probation offices. Preliminary findings present new perspectives on current debates. Approaches of holistic women's centres are looked at alongside those of probation. The paper argues that, rather than imposing a probation framework onto these voluntary organisations, it is their philosophical underpinnings and structures, placing individuals' social needs at the forefront of practice with women and supporting practitioners to do so, which should be adopted formally within probation settings—Community Rehabilitation Companies (CRCs) and the National Probation Service (NPS).