This research investigates capacity building initiatives in developing countries’ ability to aid in a transition toward sustainability. A key system, the education sector, enables and creates human capacity. Teacher Training Initiatives (TTIs) are an organized effort to build the capacity of teachers within the education sector. Information and Communication Technologies (ICT) are a rising addition to TTIs that can expand the network, knowledge-sharing, and communication potential of TTIs. Yet, is this growing trend aiding in building capacity at the expense of long-term sustainability? Utilizing the Framework for Strategic Sustainable Development, this research employs literature reviews, interviews, data analysis, workshop participation, and an expert panel to illuminate how ICT enabled TTIs can contribute to sustainability. An intervention in the current planning process was identified as a key leverage point to shift the system toward sustainability. Taking a whole systems perspective when planning initiatives better equip stakeholders to build effective programs today that will not compromise the capacity building of the future. This upstream approach may build the foundation to move toward a strategic ICT enabled TTI, but it is not the only major factor. ICT enabled TTIs function within complex systems, requiring ongoing strategic planning and management toward sustainability.