This article studies technology driven, development focused initiatives [ICT4D projects] at a community level in South Africa. This study forms part of the existing debate on ICT4D project success, and suggests answers towards accelerating ICT4D projects’ growth towards maturity and sustainability. Concerns that receive attention include the level of ownership and control taken by members of benefiting local communities in ICT4D projects, the level of social embeddedness of ICT4D projects, and a revision of the concept of sustainability within the ICT4D context. A detailed case study that compares two similar ICT4D projects influencing four local communities, focusing on educational institutions within the communities in South Africa, provides the foundation for this article. Adjustments are made to the Five Stages Maturity Model for ICT projects (Leem et al., 2008) and then used to guide our critical discussion regarding each community’s relationship with the ICT4D projects currently running within each society, and how these relationships can be matured and sustained. Findings include a discussion of the importance of direct and diffused increases in freedom resulting from an ICT4D project and the often discounted role of recognition, celebration of achievements within the local community, and media involvement in the maturity, and hence sustainability, of ICT4D projects.