In Kuwait, unsuccessful attempts to use and integrate technology into classrooms and lecture halls are currently being witnessed in schools and higher education institutions. Such failure is believed to be the consequence of various challenges, such as cultural, technical and contextual challenges. In this exploratory study, the researcher has tried to shed some light on these and make recommendations on how to address them. In order to explore these challenges, the method of document analysis was applied, collecting data exclusively from documents related to the Kuwaiti context. These data were analysed using a thematic analysis approach and NVivo10. The results show that such challenges (i.e. cultural, technical and contextual challenges) exist in the Kuwaiti context and lead to the failure of E-learning projects. As a final point, a conclusion was drawn and some recommendations made and presented.