Shame is an emotion that features widely in a range of mental health difficulties. Feelings of shame are frequently elicited in the therapeutic encounter. Undetected shame may cause ruptures in the therapeutic relationship and premature termination of therapy. Despite this, the literature review suggests shame in psychotherapy has been largely under-researched. This study explores how Maltese therapists understand and manage feelings of shame evoked in the therapeutic encounter. The literature review discusses the major theories and contentions regarding shame in psychotherapy and traces the transition from viewing shame as an intrapsychic phenomenon to its effect on relationships and its presence in the wider social context. A qualitative research approach was used to explore the experience of Maltese psychotherapists. Semi-structured interviews were conducted with ten participants whose years of experience ranged between six and 28. The interviews were analysed using Interpretative Phenomenological Analysis (IPA). Four super-ordinate themes emerged: The Therapist’s World of Shame, Be-holding Patients’ Shame; A Shared Experience, and The Island of Shame. Participants portrayed themselves as highly self-judgmental and shame-prone individuals, and described their cultural context as “a breeding ground for shame”. This research illustrates the benefit of therapists’ understanding their own and their patients’ shame signals and triggers during therapy. It broadens understanding of how cultural dynamics serve to augment feelings of shame, which can lead to the loss of a psychotherapist’s sense of authenticity. This study also strengthens the evidence base regarding training and supervisory needs of trainee therapists.