Much research, training or lifelong learning initiatives have focused on closing the digital gap and increasing the digital literacy of older adults compared to younger demographics. Often, there is a strong emphasis on step-by-step instructions for specific applications and devices. However, based on previous research, we suggest that the whole socio-technical system within which older adults use technology influences their technology acceptance, confidence and uptake. Our three-year weekly engagement with an aged care provider across three care settings has unfolded the intricacies and nuances of how older adults develop an understanding of technology to decide on its use. This research proposes the co-exploration of technology as an approach to navigating through these concerns and understanding older adults’ circumstances and goals when they learn about technology. The co-exploration approach provides opportunities for the residents to be introduced to technology, experiment with it, reflect, and try it on their own time and pace. This collaborative and person-centred approach contributes to providing positive and meaningful experiences to older adults, identifying appropriate ways of introducing technology to them, and guiding them to make informed decisions on technology use. We illustrate this approach with several cases where older adults decided to use (or not to use) technology devices or tools based on a thorough understanding of them. This research has practical implications for lifestyle staff when teaching and implementing technologies in aged care settings and the need to gain awareness of residents' individual preferences and technology knowledge.