In contemporary Russia, online discourses on gender reflect the complex legacies of the Soviet and post-Soviet attitudes and approaches to masculinity and femininity. The current discourses on gender affect its digital construction. Mirroring the gendered discourses on masculine and feminine roles and patterns of behavior, digital media spaces impose similar restrictions and expectations on female users as those experienced by women in their offline activities. This chapter offers an analysis of how the World Wide Web and digital technologies influence gender identity politics in contemporary Russian society. We look at the ways Russians construct gender online, how their practices become means of resistance and activism, and how they adapt and shape digital technologies to perform their gender identities and communicate with the State in the situation of increasing surveillance and control of material and cyberspaces.