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The Affordable Care Act (ACA) was signed into law by President Obama in 2010; it undertook to address the many faults in the current healthcare system, particularly focusing on historically marginalized and underserved communities. Although the bill prohibited healthcare providers from discriminating against certain patients, the trans* community continues to face health disparities, particularly a lack of access to knowledgeable doctors and adequate health care services that address their specific needs, in addition to obtaining insurance enrollment and coverage. Although there are undeniably certain loopholes and inconsistencies that detract from the bills purpose, the main culprit behind the continued discrimination is not insurance policy but rather the conceptualization of gender in Western society. By adhering to a strict binary gender system, social institutions and mainstream society codify discrimination again people that identify outside of this dichotomous labelling classification. In the last few decades, there has been a promising trend toward tolerance of the LGBT community and particularly a movement toward sharing the non-standard narratives. This thesis took advantage of that opportunity to speak to trans* individuals about their health care experiences with doctors, medical treatments, insurance companies, and a more general description of their transitional process, in whichever point they were currently experiencing. In addition to providing an analysis of the current situation, this work hopes to inspire the reader to question their fundamental conceptions of gender to help create a more open-minded society for all people.