Teaching today relies a great deal on IT resources and there are many schools opting to digitize they curriculum i.e. change the traditional style to what has recently been coined as “Smart School” style, in which ICT plays a significant role. The Smart School initiative seeks to enhance education in a smarter and more innovative way using ICT. The purpose of this study is (1) to explore the challenges faced during the implementation of smart schools from the perspectives/viewpoints of the service provider, teachers and school IT administrators; and (2) to provide a set of recommendations to minimize such challenges. In order to achieve the research objectives two case studies were conducted among schools that had already started implementing the process of becoming smart schools. Both case studies included a set of interviews with schoolteachers, the people in charge of the proposed project, school IT administrators and a service provider. In addition, there were sets of classroom observations conducted in the respective schools. Study results and the examination of data analysis revealed that there are many challenges faced by the perspective parties and these challenges are discussed in some detail. The researchers then provided a set of recommendations to minimize, or indeed to overcome the challenges encountered in becoming a Smart School in Oman.