Language policy and usage in the post-communist region have continually attracted wide political, media, and expert attention since the disintegration of the USSR in 1991. How are these issues politicised in contemporary Estonia, Latvia, and Ukraine? This study presents a cross-cultural qualitative and quantitative analysis of publications in leading Russian-language blogs and news websites of these three post-Soviet states in the period from 2004 to 2017. The most notable difference observed between Ukraine, on the one side, and the two Baltic countries, on the other, is that many Russian-writing users in Ukraine’s internet tend to support the position that the state language, i.e. Ukrainian, is discriminated against and needs special protection by the state, whereas the majority of Russian-speaking commentators on selected Estonian and Latvian news websites advocate the establishment of Russian as a second state language. Despite attempts of Ukraine’s government to ukrainianise the public space, the position of Ukrainian is still perceived, even by many Russian-writing commentators and bloggers, as being ‘precarious’ and ‘vulnerable.’ This became especially visible in debates after the 2013–2014 Revolution of Dignity, when the number of supporters of an introduction of Russian as a second state language significantly decreased. In the Russian-language segments of Estonian and Latvian news websites and blogs, in contrast, the majority of online users continue to reproduce the image of being ‘victims’ of their countries’ nation-building. They often claim that their political, as well as economic rights are significantly limited in comparison to ethnic Estonians and Latvians. This book illustrates that—notwithstanding variations between the Estonian as well as Latvian cases, on the one hand, and Ukraine, on the other—there is an ongoing process of convergence within Ukrainian debates if compared to those held in the other two countries in terms of an increasing degree of ‘discursive decommunisation’ and ‘derussification.’