Since the enrolment of its first cohort of students in 2009, the University of Botswana School of Medicine (UB SoM) has employed elearning as a key element to support and strengthen its model of decentralised medical education. Significant investments have been made in setting up the physical infrastructure, and in acquiring relevant expertise to develop and implement an elearning agenda in a context with practical challenges associated with medical education in decentralised setup. Following the enrolment of its first cohorts of medical students, and residents in Paediatrics and Internal Medicine between 2009 and 2010, the School also launched a Family Medicine training programme in 2011 at two rural sites. With the expectation of contributing to a positive teaching and learning environment for faculty, residents, and medical students in these remote areas, elearning is also seen as important for their retention, and thus for improved access to quality health care in rural Botswana. In this paper, the authors critically reflect on the strategies used to implement elearning at UB SoM over the past 18 months, and highlight challenges experienced while implementing elearning in a new medical school situated within an older university context. Strong relationships with partners were identified as a critical foundation for the long-term sustainability beyond the initial procurement and installation infrastructure. While confirming the obvious technical challenges in a setting like Botswana, the authors emphasise the need not to underestimate associated broader challenges in engaging a diverse range of users, partners and stakeholders; not to lose sight of the pedagogical goals that are meant to drive the choice and use of technology (rather than vice versa); and to ensure that the expected benefits of the technology can and will be shared and sustained by a range of partners in the long run.