Even though Kenya holds democratic elections as understood by the definition of democracy, technology has allowed the government to manipulate and control information, and author political thought in favour of desired candidates. Central to the Western liberal idea of democracy are elections, the exercise of political choice and freedom. By and large, elections are regarded as a true “democratic exercise” under the presumption that, through them, the people have a say in how their country will be governed. What is worth noting, however, is that elections must be free and fair to ascertain the political freedom required under the tenets of true democracy. This idea of free and fair elections is cemented in the Kenyan constitution. Despite this, in Kenya, though governments are elected by citizens every five years, the country has a deep-rooted history of authoritarian electoral practices which impugn its democracy. Such authoritarian electoral practices are what led to the Kenyan Supreme Court’s historic decision to annul the 2017 presidential general election. Willy Mutunga, Kenya’s Chief Justice at the time, described Kenya as a “fake democracy where elections do not matter because the infrastructure of elections has been captured by the elites.” Kenya is representative of a nation where elections do not equate to democracy, and technological advancements have only provided the government with leverage over its citizens’ political choice. Kenya gained independence from the British Imperialist Empire in 1963, determining itself a multi-party republic in 1964, and since then the authoritarian legacy of colonialism has lived on. The most significant demonstration of this is the fact that, since independence, not a single sitting president has ever lost an election. Moreover, despite the apparent change in politics, Kenya’s former authoritarian ruling party (Kenya African National Union, KANU) still heavily influences today’s politics. The country is yet to elect a president or vice president who wasn’t a member of KANU; further, a considerable percentage of cabinet appointments and nominees have been former KANU office holders. This demonstrates that, though power in the country appears to be switching hands, the country’s democracy still remains captured by a class of oligarchs. The country’s first president Jomo Kenyatta banned the first ever opposition party formed by his then deputy Odinga. The government then ruthlessly repressed political dissent, and laid the foundations of authoritarianism in Kenya’s electoral future. Although the 1990’s saw the re-establishment of multipartyism, subsequent elections were undermined by electoral interference akin to the authoritarian political origins of the country. No matter who was running, it would become expected that elections in Kenya would be tainted with rigging, state sponsored violence, voter intimidation, political assassinations and gagging the press. This assessment casts political freedom and individual choice as illusionary within the context of a Kenyan election. It appears that at the ballot Kenyans often think that they are making a free political choice when they are not. Interference, corruption, and autocracy are symbolic of Kenyan elections, unfortunately. With a majority of Kenyans now connected to the internet, it would only be expected that the old methods of electoral interference have been adapted to make the most of these new age technologies. The most paradigmatic illustration of this is the 2017 murder of Chris Msando, who was the top ICT officer of the country’s election commission. The man whose responsibility it was to safeguard the security of the electronic system was discovered tortured and murdered a week before the election. Many people believe that the government is the major suspect in the murder, which remains unsolved. The fact that a majority of the Kenyan population has access to the internet and half the population is active on social media is a new reality that creates great potential for authoritarian electoral practices on an unprecedented scale. In 2013 and 2017, personal data belonging to millions of Kenyan Facebook users was mined without their consent by Cambridge Analytica to help former President Uhuru Kenyatta win the elections. Using ominous attack commercials that misrepresented rival presidential candidate Raila Odinga as violent, dishonest, and dangerous, the political choice of voters was manipulated and swayed. This demonstrates how Facebook, Twitter, Google, and other digital firms who hold user data, can be used to influence elections.