In this chapter, we report research investigating interactions of practitioners and adults with mental health conditions where the latter are judged to be resisting, contesting, or evading treatment. During the last 15 years, we have conducted various studies examining the discursive practices through which practitioners make sense of and respond to those with whom they work, focusing especially on situations in which individuals are considered difficult to manage. Our main purpose has been to better understand the practices by which the mental health disciplines seek to regulate service user expectations and behaviours in light of the discourses that inform them, especially those arising from the social justice and human rights concerns evident in recent mental health policy both in Australia (Australian Parliament Senate Select Committee on Mental Health, 2006) and internationally (UN, 2006). Much of our work in this area has involved practitioner interactions with people living with borderline personality disorder (BPD). In what follows, we begin by outlining the current policy and practice context in Australia. The remainder of the chapter discusses a number of studies in which we have investigated interactions between health practitioners and people living with BPD or other forms of severe prolonged mental illness.