A growing body of research on state-sponsored social media actors has raised concerns over attempts by hostile states to influence public opinion online. The annexation of Crimea is one of such high-profile cases, in which Russia was accused of using media technologies for influencing Western publics. We use Twitter’s and Clemson University’s Anglophone and Russophone data on Internet Research Agency (IRA)-affiliated actors (‘Russian trolls’) and compare it with the ‘non-troll’ Tweets. We take a mainly linguistic perspective and analyse diachronic meaning changes through collocation analysis. We use quantitative computational tools for data collection and keyword identification, as well as qualitative Fairclough’s Critical Discourse Analysis and tools of Systemic Functional Linguistics to analyse two crucial aspects that are not dwelled on in previous research on the annexation of Crimea – the annexation as a pivotal moment that reshaped Russia’s social media landscape and Russia’s turbulent societal and social media environment after the annexation, which created fertile ground for language change. We argue that that most IRA’s troll tweets align with the overarching Kremlin’s narratives about the annexation, however there are some significant departures from this general ‘baseline’, which are thoroughly examined. The use of language observed is strategic, and the changes in language use indicate the important differences between ‘troll’ and ‘non-troll’ accounts.