In this study the authors investigate the challenges facing the provincial department of education with respect to the e-Readiness of secondary school teachers in the Province of KwaZulu-Natal, South Africa. The study is based on a sample of the secondary schools in the Ethekwini Municipality. The results indicate that any ICT interventions by the provincial Department of Education are bound to fail unless other non-technological interventions are put into place first. We show that where the ICT interventions are needed the most, the teachers are least prepared to receive it. Thus we conclude that instead of making short-term political decisions, the Department must first embark on a medium to long term plan to first make the environment amenable for an ICT intervention. These would include large-scale school upgrading, teacher training and retention plans to keep experienced and qualified teachers within the schooling system.