While many transgender and gender diverse individuals rapidly achieve amenorrhea on testosterone, emerging data has identified that breakthrough bleeding (BTB) can occur in up to one third of individuals with long term use. BTB can worsen dysphoria and patients may seek management to reattain amenorrhea. Because of this, there is a need to assess efficacy of management approaches. The primary aim of the study was to evaluate methods used by patients and their providers to manage BTB which arises after one year of testosterone use. Secondary aims included describing the diagnostic approaches to BTB, and proposing an algorithm for classification and management of BTB in this patient population. This was an IRB-approved single tertiary center, retrospective chart review of transgender and gender diverse individuals on testosterone gender affirming hormone therapy who experienced BTB after one year of use. Charts were reviewed to determine patient characteristics, testosterone use, and BTB management approaches. Of the 96 individuals who had been on testosterone for one year and experienced BTB, 97% (n=93) engaged in at least one approach to management. The mean age at initiation of testosterone was 21.9 (SD 5.4) and the median duration of time on testosterone was 54.5 months (IQR 33.5,82). Only 16% (n=15) were using menstrual suppression at the time of their BTB episode. BTB was successfully managed in 77 (79%), following between 1-4 attempted approaches. More than half of management attempts (63%) were successful on the first try. When management approaches were analyzed independently, the range of success associated with any particular approach was between 33-100%. Other than hysterectomy, which was fully successful at managing BTB, no approach was significantly better than no intervention. This was true both for individuals who did and did not bleed with missed testosterone doses. Regardless of what approach was used, after a failed attempt, the next attempt was successful in more than half of individuals. Of the 16 who underwent hysterectomy, one did so in part as a first line approach to manage BTB. In this study, use of medical management methods was not found to be superior to observation alone in the management of BTB. In the absence of data supporting superiority of any method, we recommend tailoring method attempts to patients' goals.