The relationship between media freedom and the individual right to free speech is a complex and nuanced one, such that the former should not simply be conflated with the latter. A number of high profile cases have demonstrated that expressing opinion on social media can be subject to criminal prosecution. Before shedding the light on the Kuwaiti courts’ approach to penalizing political opinions published on twitter and comparing the Kuwaiti court decisions to British court decisions in similar cases, this paper will begin with understanding the concept of liberty, the difference between liberty and human rights, the source of liberty and the danger of using the harm principle, the caretaker and the utopia principles to issue laws which may appear ostensibly to protect people but curtail the important freedom of expression instead.