This chapter explores some of the complex interpersonal aspects of clinical work on the staff–patient interface in women’s forensic services. Suggestions are made as to how understanding this particular complexity can inform subsequent clinical interventions. The chapter is informed by considerable clinical experience of women’s forensic services and from the vantage point of multiple roles, including nurse, psychotherapist, teacher, reflective practice group facilitator, supervisor, researcher, manager and leader. The task of front-line workers in services for women offenders diagnosed with personality disorders is rarely experienced as straightforward. Indeed, without specialised training and support, staff whose work bases them in the social environment of services often find themselves feeling bewildered by the perplexing array of behaviours the women engage in. Even when working in a proactive and integrated way, this clinical work is emotionally difficult.