It has long been demonstrated that psychological and psychiatric fields pathologise and discipline certain bodies. However, few have explored practitioners’ resistance to, and critiques of, gender oppressive practices. Drawing from theoretical frameworks of transgender studies and queer theory, this paper reports on qualitative data gathered from semi-structured interviews with six therapists in Sydney, Australia. Case studies highlight the ruptures, dissonances, and possibilities of transgender and gender diverse (TGD) mental health care in practice. Thematic analysis of therapist case studies demonstrates how notions of “allyship” are inadequate in problematising power dynamics, binary gender, and cisgenderism, as therapists engaged in problematic discourses and practices in relation to their TGD clients. Exploring the limitations of traditional gatekeeping models, the paper situates counselling and psychotherapy practices within an Australian context as holding unique opportunities to engage in anti-oppressive practice with TGD clients. The research makes clear that active frameworks for challenging oppression in the lives of clients are essential to ethical, client-centred work.