The current global scenario of hyper-connectivity, technology change, and social change make it necessary to rethink the vision and methods employed by governments, development agencies and the private sector to impulse socioeconomic development through the adoption and application of Information and Communication Technologies (ICT). We pose that the availability of computing and telecommunications infrastructure, highly converging devices for Internet access and content suited to the population needs and idiosyncrasies are not enough to accomplish long-term socio-economic development. The method employed in this contribution is focused on the principles of complex adaptive systems. The objective is to develop an operational framework to support the planning and design of digital inclusion projects integrally. The proposed framework emerges from the application of two complexity perspectives: Organized Complexity and Post-Normal Science. We argue that it is key to study the interplay of innovation, development, and ICT for each particular context to acquire deeper insights and understanding of the elements, both human and technological, affecting the dynamics and long term sustainability of digital inclusion initiatives, particularly in the era of Artificial Intelligence and related emergent technologies.