For over a decade, Ukraine has been beset by Russian military incursions, hybrid and hot, and the populace has faced the leadership of the country in two revolutions over two decades (Orange and Euromaidan or Revolution of Dignity) as it has sought to ensure democracy and a European future for the state. To best understand the role of culture and social forces, we shall examine how political and online culture converge to militate for resistance to external aggression or political change within. A review of both Ukraine’s history and that of technological change, it is evident that new communicative mediums were quickly harnessed to disseminate information as well as contest power structures. These innovations shaped both the creation and sharing of memes as well as video footage and other cultural creations. Such cultural acts can be tied to traditional folklore as they are often anonymous creations widely distributed and tied to a given social and cultural understanding of the world. Ukraine shall be used as a case study to see how its recent history was shaped by the evolving online landscape. We will examine how Ukraine’s social and political evolution both paralleled and differed from other global events, notable the Arab Spring among others, when it comes to the use and importance of the internet and social media. These new technologies enabled actors to circumvent tightly controlled traditional media such as newspapers and television, to broadcast information both local and globally. The challenge now facing popular movements is not access to information, but rather the proliferation of “fake news” and often state-sponsored trolls whose aim is to quickly share disinformation online. This leads to as will be discussed to meme wars which seek to win online hearts and minds.