As technology continues to permeate most aspects of our lives, many older adults face the need to improve their digital skills to avoid social isolation and exclusion from essential services. With the global older adult population projected to reach 16% by 2050, there has been a renewed urgency to address this growing digital divide. However, many existing digital literacy initiatives are often inaccessible or not optimised for touchscreen devices such as tablets, which have risen in popularity among older users. Moreover, the assistance provided by their support networks often serves as a temporary fix until a new issue arises, leading to a cycle of dependency. This pilot study aims to explore how older adults’ digital literacy and social connectedness can be improved by leveraging intergenerational exchanges. It offers insights into the experiences of older adults with technology, how younger people in their lives assist them, and the means by which both groups stay connected. As part of a user-centred design process, we conducted small but in-depth user studies with older adults, along with an online survey targeting younger individuals. Our findings, combined with research into accessible UI/UX design, led to the development of EldersOnline, an age-friendly platform that fosters personalised learning through intergenerational exchanges. While participants in our user studies responded positively to the platform, further research is needed to adapt these solutions to other aspects of older adults’ lives and to account for cultural differences. Such approaches could help bridge the global digital divide and encourage healthy ageing among older adults.