This paper examines the change drivers and challenges involved in the transitioning of the Water Research Commission’s Amanzifor Food training of agricultural educators and farmers’ face-to-face co-engaged course to an online course aligned with Education for Sustainable Development (ESD)(www.amanziforfood.co.za).The study drew on system thinking to analyse components within the course development activity system. Insights from stakeholder engagement and expansive learning processes fed intokey emergent themes which informed the e-learning processes. The research highlights how the development and implementation of a sustainable training programme using Information and Communication Technology (ICT) tools bring together learning processes occurring within different interconnected dimensions and in complex and unpredictable ways. It became clear that to utilise e-learning as a mediating artifact capable of facilitating social transformation towards suitability expansively,certain conditions needed to be in place. The drivers that impacted the development of e-learning as a mediating tool included the need to find an alternative learning platform for broader dissemination of Rain Water Harvesting &Conservation(RWH&C) knowledgeand alignment with the United Nations Sustainable Development Goals(SDGs). This study concludes that this transition requires specific tools, adequate time, an understanding of e-learning pedagogical processes and learning platform functionalities (requiring upskilling of the digital literacy of the development team and other actors),and workable data-efficient or data-free, smartphone-friendly training and communication platforms.