The vocal arts have historically relied on binary and often rigid classifications for singing voices. However, the increasing visibility of transgender singers challenges these traditional frameworks. This study investigates the complex question of how to classify transgender singing voices, acknowledging the potential for such classifications to be reductive or harmful to the individuals involved. This qualitative and exploratory investigation employed a multi-phased approach. The first phase involved practical training with a specialized phono-audiologist focused on transgender speech voices, followed by interviews with their clients to gain insight into vocal transition experiences. The second phase consisted of a month-long workshop designed for transgender singers, which served as a practical exploration of vocal techniques. Data were further enriched through in-depth interviews with the workshop participants. While the study did not lead to a definitive classification system, the findings reveal a more nuanced and sensitive issue: the act of classifying transgender singing voices risks placing individuals and their unique vocal expressions into limiting 'boxes.' The process of vocal exploration and self-identification among participants suggests that traditional classifications may not adequately capture the diversity of transgender vocal realities. Participants' experiences highlighted a strong preference for vocal self-determination over external categorization. This research suggests that a shift from rigid classification to a more flexible and affirming approach is necessary when working with transgender singing voices. Instead of seeking to categorize, the focus should be on empowering singers to explore their full vocal range and express their identity authentically. The study’s primary contribution lies in highlighting the ethical and practical limitations of traditional voice classifications and advocating for a more person-centered, non-binary approach to vocal pedagogy.