Crowdfunding websites have gained immense popularity as a strategy for transgender people to raise money for transition-related medical care. Even with recent successes in gaining insurance coverage for expenses related to trans-specific healthcare, many trans and gender-nonconforming people face significant out of pocket expenses for medications and surgical procedures. While acknowledging the important function it serves in many trans people’s lives, this project calls for a critical inquiry into the politics of crowdfunding for transition related care. Who is most likely to turn to crowdfunding, for which expenses, and to what success? What forms of sociality does crowdfunding foreclose, and what forms does it enable? How might crowdfunding work against a liberatory trans political project? Using descriptive statistics and content analysis of trans healthcare fundraisers on the website, I illustrate how campaigns reproduce normative transition narratives, privatize inequalities, and support neoliberal logics. Although trans people crowdfund for a variety of transition related needs, the majority of online campaigns are used to fund transmasculine chest surgeries. With the exception of individuals with a high degree of visibility or popularity in (generally urban) queer and trans communities, most campaigns fall dramatically short of their fundraising goals. In addition to utilizing medically sanctioned narratives of “being trapped in the wrong body,” campaigns privatize inequality by failing to acknowledge their collusion in a neoliberal project. I conclude with a consideration of how to incorporate a “revolutionary etiquette” of crowdfunding for transition healthcare.