This paper reports on a PhD study, investigating the supervision of women service users (WSUs), by women probation officers (POs) based on video data of one-to-one supervision sessions. The research identifies competing agendas of probation in England and Wales - one side emphasises punishment, whilst the other encourages humanistic, relationship-based practices. POs, routinely juggling these opposing expectations, appreciate traditional probation values of giving the WSU a voice and embracing psychodynamic approaches, to provide structure and support in confronting the complexities of officer/service user interactions. However, the data show that driven by managerialist enforcement requirements, it is the punitive discourse which is more frequently translated into practice. Organisational pressures, feelings about the person opposite, the offence or the individual’s background can manifest as conscious or unconscious micro-messages or masking messages. Just as SUs put on masks to disguise negative emotions or feel powerful, so too do POs; POs recognise masks and deceptions in SUs and, similarly, SUs are aware of this dynamic with POs. The research identifies practitioner ambivalence to certain narratives, particularly sexual abuse or poor mental health and, it is argued, reflective supervision is needed to deconstruct difficult personal and professional issues.