Purpose: It has been widely noted that existing healthcare systems do not always function effectively for the transgender population. Despite existing healthcare barriers, however, transgender individuals have been shown to have positive healthcare experiences. This study explored a cohort of transgender individuals who had positive healthcare experiences, and those who were involved in creating a positive healthcare experience for transgender individuals.Methods: A single case study was conducted, which included 10 interviews with transgender individuals, healthcare providers, and friends/family/significant others of transgender individuals. Data were analyzed through thematic analysis.Results: Seven key themes emerged within macro levels (large-scale system), meso levels (local/interpersonal), and micro levels (individual/internal) of healthcare system support. At a macro level, few system strengths were shown, with hope for change in the future. On a meso level, both external supports and informal networking emerged as key factors in positive healthcare experiences. At the micro level, self-navigation, characteristics for success, and personal strategy development were important for achieving positive experiences.Conclusion: Factors that contribute to positive healthcare experiences for transgender individuals were outlined in this study, showing that meso and micro level support compensate for large-scale healthcare system deficits.