This article aims to discuss some of the factors that compromise the efficacy of digital inclusion educational projects in communities with elevated social vulnerability, based on the evaluation of an unsuccessful experience. The influence of some external parameters (social, political, cultural, and technological) have been analyzed, which have potentially created chasms between the theoretical discussion and the true reality likely to be encountered in the majority of the public policies and programs concerned with digital inclusion. The polemic related to failure, the role of each of the participating sectors (educational institutions, local communities and society in general) have also been analyzed. The relevance of the synergy that these projects must have has been considered as well in order to ensure that the implementation of educational initiatives in digital community spaces truly has their intended social relevance.