Fertility-preservation counseling in the transgender patient population is recommended by multiple organizations, including the American Society for Reproductive Medicine, the World Professional Association for Transgender Health, and the Endocrine Society. The optimal time to pursue fertility preservation has not been established, and data on potential effects of testosterone therapy on future reproductive potential are limited. This Current Commentary seeks to elucidate the most appropriate time to perform oocyte cryopreservation in relation to time on and off testosterone therapy, age of the individual, and emotional effect of treatment. Although there have been multiple studies that have demonstrated successful oocyte cryopreservation regardless of testosterone exposure, the data on live-birth rates after oocyte cryopreservation are limited. Moreover, the process of oocyte cryopreservation may have a significant negative emotional effect on the transgender male given the feminizing effects of gonadotropin stimulation, as well as the invasiveness of pelvic ultrasonograms and the oocyte-retrieval procedure. With our review, we demonstrate that a comprehensive, individualized approach to fertility-preservation counseling and timing to pursue treatment are essential. Postponing fertility-preservation procedures until patients have reached early adulthood might be considered to avoid the potential effect on mental health, without compromising outcomes.