This article focuses on the story of one transfeminine (transgen, in local parlance) wedding singer, Shabu, identifying through interviews, observation, and song analysis the possibilities of self-expression for transgens as well as for cisgender women who attend these performances. How have they carved out agency for themselves amid Kashmir’s territorial conflict over its sovereignty? The article demonstrates how Kashmiri gendered futures are intimately tied to courageous and innovative performances in women’s spaces, even within pronounced systemic constraints. Shabu’s songs concern women’s agency, gender dynamics and roles, family relationships, and gender presentation both in and outside women’s familial household and community/kin networks. The songs both embody accepted tradition and open doors to innovation, protest, and political commentary. The digital life of these performances on YouTube has contributed to their dissemination and popularity. This article addresses questions arising from shifting contexts of transgens’ wedding-song performances and contributes to the body of analysis of digital folklore through decolonial feminist and queer folkloristic lenses.