A growing body of international evidence suggests that sex workers face a disproportionate burden of violence, with significant variations across social, cultural, and economic contexts. Research on trans sex workers has documented high incidents of violence; however, investigations into the relationships between violence and social-structural contexts are limited. Therefore, the objective of this study was to qualitatively examine how social-structural contexts shape trans sex workers’ experiences of violence. In-depth semistructured interviews were conducted with 33 trans sex workers in Vancouver, Canada, between June 2012 and May 2013. Three themes emerged that illustrated how social-structural contexts of transphobia and criminalization shaped violent experiences: (a) transphobic violence, (b) clients’ discovery of participants’ gender identity, and (c) negative police responses to experiences of violence. The findings demonstrate the need for shifts in sex work laws and culturally relevant antistigma programs and policies to address transphobia.