Discrimination against transgender individuals is more than a social issue; it is a health issue, and a global epidemic at that. The fear, hatred, and general ignorance with which the current cisnormative society approaches transgender individuals creates significant barriers to accessing quality healthcare. While interacting with healthcare providers transgender individuals face a myriad of discriminations ranging from microaggressions to outright assault. These interactions, which at best deter transgender individuals from seeking medical attention and at best put their lives in danger, have been termed by the transgender community online as “Trans Health Fails.” In 2015, the organization MyTransHealth posted on Twitter asking for transgender individuals to share their #TransHealthFails. The ensuing 3,000+ tweets in this hashtag provide a valuable look into the health inequity transgender individuals face. This research takes the form of a retrospective longitudinal analysis, examining tweets in the hashtag from July 30th 2015 to July 30th 2018. Grounded coding was chosen as the analytical approach so as to allow the experiences of the individuals to speak for themselves, rather than imposing the researcher’s own ideas.