The article analysis paradoxes of governmental regulation of blogging in Russia based on the case of legislation for bloggers, which was adopted as law in 2014 and is known as the “Bloggers Law”. From the beginning, the law has been criticized by Western media and liberal opposition in Russia as restrictive towards the freedom of speech in the Russian Internet. The case has been analyzed with public policy analysis approach, including precise examination of policy aims, implementation, and results. The authors analyze all fourteen trials in Russian courts which tried to enforce the law. Due to complete inapplicability of the law, it has been quietly repealed by authorities in 2017. The authors argue that this case indicates complicity and in-linearity of media system development in Russia, reflecting national problems with controlling the global digital communication.