This article reports on an e-learning readiness study that was carried out to assess the organizational and individual factors of the two major stakeholder groups (teachers and students) in the secondary education institutions in the State of Kuwait in order to provide significant information to the policy makers and regulatory bodies for the development of successful e-learning strategies. Data were gathered with the use of the e-learning Readiness Survey from a purposive sample of 1,314 teachers and 1,307 students. This study looks specifically at some factors at the initial stage of an e-learning introduction that can have tremendous impact on the later stages of the process. The findings from the study were instrumental in implementing successful e-learning strategies for Kuwait and will also benefit e-learning initiatives in similar institutions in other Gulf Cooperation Council countries and beyond.