Much of the ICT facilities in developing countries' educational institutions are not used and ICT for Development projects have high rates of failure. The reasons for this phenomenon are structural and embedded in the very fabric of the Cooperation & Development project management practices. Bureaucracies' requirements, transaction costs, sustainability concerns, mutual perception and identity negotiation between “developer” and “developee” and above all, a mechanistic mindset for both education and reality in general, are crucial factors in shaping the project implementation, often in contrast with the public rhetoric about it. The role of technology in this complex dynamic is addressed critically, pointing out some structural reasons for its failure to deliver the expected benefits in the mid-long run, namely: the industrialism burden, the daily digital divides and the omission of maintenance. A radical change of mindset is called for, one to be applied both to aid and education.