As population ageing is observed globally, and technology continues to expand into most parts of our lives, many older adults face challenges in adapting to a world that they feel unprepared to inhabit — one filled with increasingly intertwined and fast-evolving technologies that have become necessary to fully participate in society. The age-related digital divide, caused by the gaps in access, motivation and skills of many older adults to use digital technologies compared to younger people, is now a significant problem for the wellbeing and independence of older adults and requires urgent solutions. Increasing the digital literacy and confidence of older adults may help reduce this gap. However, effective strategies for improving digital literacy in later life must take into account the needs and preferences of older learners. This paper reports on two pilot studies conducted to create and evaluate prototype digital literacy resources to discover effective forms and content. This wo rk draws from literature, related work, and feedback on our prototypes from older adults in local communities. Our findings indicate that older adults often prefer device and task-specific digital literacy resources in printed form as a familiar medium before progressing to digital learning, and value community involvement in ongoing support for the learning process. Resources that use figure-of-speech based language and informative diagrams can also be beneficial to older adults, particularly when learning novel digital tasks. These preliminary insights also highlight the potential for conflicting requirements from a diverse demographic and the need for further exploration of the topic