Building on previous trans YouTube scholarship, this dissertation is based on a content analysis of two digital activism projects: 1) #WeHappyTrans*, a compilation of 59 YouTube video responses posted between 2012 and 2018, and 2) #TheGenderTag, a compilation of 704 YouTube video responses posted between 2016 and 2019. By analyzing the audio and visuals of a subsample (N=80) of these two archives using theoretical and emerging codes, I identified key themes as relevant to digital activism effectiveness and well-being. I discuss implications for policy, public health, healthcare, and community organizing in the conclusion. Contrasting prior medical sociology literature that is not presented from the perspective of trans people and primarily focuses on negative aspects of trans lived experience, I have employed a transfeminist methodology that centers self-definition and self-determination. My methods are heavily informed by transnormativity and intersectionality scholarship. In addition to providing an example of how transfeminist methodology can be applied in the context of digital media, this dissertation fills a crucial gap in literature focusing on qualities of trans lived experience that contribute to increased QoL. My hope is that the findings of this study will be considered collaboratively between scholars and activists in many contexts, including within the growing fields of health informatics technologies and trans public health. The findings of this study are also relevant to several ongoing discussions within the fields of sociology, public health, cultural and media studies, and queer and trans theory.