Abstract: Shadow mass-literature online libraries in Russia developed during the early Post-Soviet years. They are a phenomenon rooted in both the practice of circumventing constraints caused by state censorship, and a book production process of insufficient quality. Since the fall of the USSR, Russian legislation has aligned itself with international standards, adopting their strictest instantiation. In 2013, “anti-piracy” legislation made “information intermediaries” responsible for illegal content, introduced an “eternal” blocking of sites, made pre-trial negotiations more difficult. Successive amendments have sought to respond to the circumvention tactics developed by shadow libraries. In this context, for a library which is not part of the book market, remaining in the legal realm means freezing its own content or becoming a self-publishing platform. Libraries that become illegal have to ensure the sustainability and growth of their collections by multiplying their dissemination means, to provide personal security to administrators through a “safe” geographical location or strict anonymity, and to guarantee an access to their collections on the Russian Federation territory through inventive circumvention techniques. They leave the public struggle against state and industry regulation of the Internet to digital rights advocates, and promote a particular vision of “freedom” anchored in the mastery of technical tools and in uncensored cultural practices.