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The diagnostic category of social anxiety disorder (SAD) is one that is widely drawn upon in mental health settings; SAD is primarily characterized by a marked fear of social performance situations and possible scrutiny by other people (American Psychiatric Association [APA], 1994, 2013). The current study aims to explore the experiences of people diagnosed with SAD. Psychoanalytically informed research interviews, drawing on psychoanalytic ideas around the parameters of engagement and levels of engagement and analysis, were carried out with 4 male and 2 female participants with diagnoses of SAD. Four themes emerged strongly, reflecting the content and process of interviews: “A Critical Voice,” “A Passive Presence,” “Failure to Launch,” and “Behind the Mask.” These emerging themes and the overall findings are conceptualized through a Winnicottian lens, emphasising the role of the good-enough mother and facilitating environment in the struggle of participants to achieve an experience of individuation as well as authenticity with others. Theoretical, clinical, and research implications are discussed, including the need for clinicians to consider the role of early parent-child dynamics and the overall home environment and what these have left in the here and now for people presenting in this way, particularly in the way services are used and the therapeutic relationship develops. Further research into underlying dynamic issues in the origins and maintenance of social anxiety is proposed.