Gay, bisexual and other men who have sex with men (GBMSM) represent a key population disproportionately affected by HIV in various settings. While past studies have investigated how individuals negotiated their identities following their diagnoses of HIV, an emerging area of inquiry considers the implications of viral suppression, or becoming undetectable, on identity and well-being in an undetectable = untransmittable (U = U) era. We conducted 24 in-depth interviews with a purposively recruited sample of GBMSM living with HIV in Singapore. Interviews were analyzed through inductive thematic analysis. Participants viewed viral suppression as a clinical objective, and contrasted this with becoming undetectable as an identity and aspiration. Many participants saw becoming undetectable as a turning point for them post-diagnosis, and expressed a sense of achievement upon attaining the status. Participants shared that being undetectable was associated with several positive outcomes in coming to terms with their HIV-positive diagnoses that signified achievements in health, personal and social responsibilities, as well as equity in romantic and sexual relationships. The results of this study highlight the importance of becoming undetectable and its potential impact on the quality of life for GBMSM living with HIV.