The 21st century is characterised by two defining trends: the rise of ubiquitous computing and population ageing [1]. Digitalisation offers opportunities for older adults (OA) to retain an active role in their lives and alleviate the ‘burden of care’ associated with ageing. Yet, digital engagement is consis- tently cited to be inversely related to age. Although interventions to enhance the digital literacy of OA through formal in-person training have emerged, there has been little evaluation of their effectiveness. This paper presents insights into the attitudes, needs and challenges of OA in becoming digitally literate. We conducted preliminary user studies with OA and a survey of younger adults (YA) to understand their role as an informal support system. Based on these insights, we propose an innovative approach to digital literacy training for OA by combining a senior-friendly learning management system with informal inter-generational learning. A preliminary evaluation of the system yielded positive feedback and indicates a need for a more extensive exploration of the digital experiences and requirements of OA and the influence of social support systems in their digital engagement process.