This chapter examines the origins of contemporary Russian authoritarianism through the lens of the LGBTQIA+ experience. For Keenan, the status of queerness in Russian society is a useful index for more general fluctuations in the freedom of self-determination and expression. As the rigid, oppressive structures of late-Soviet life gave way to the openness and self-discovery of the 1990s, new selfhoods and self-presentations flourished. Assertions of fluidity and pluralism in post-Soviet media not only challenged earlier gender binaries and sexual mores, but expressed the broader spirit of excitement and anxiety that suffused the evolving Russian public sphere. In the 2000s, it was precisely the privileged position of sexuality as a potentially ungovernable form of personal expression that rendered it the synecdochic target for the hostility of proudly illiberal and anti-Western forces.