Older adults' engagement with information communication technology (ICT) can enhance their wellbeing and quality of life. However, older adults continue to lag behind their younger cohorts' ICT use, and many remain unconnected. While policy and strategy has tended to focus on the need to equip older adults with technology skills and improve their digital literacy, the relationship between skills adoption of technologies is not straightforward. This study sought to investigate via case study the diverse digital experiences and motivations of 10 older adults within a regional area of Queensland, Australia. Through "questerviews," the integration of questionnaire items (on technology acceptance models) and semi-structured interview questions, the participants relayed their frustrations, successes, strategies, tools and connections they needed in order to use ICT more extensively and more effectively. What these data showed were older adults with varying degrees of ICT skills and diverse motivations, from complete yet passionate beginner, through to others who were considered savvy users. Higher levels of digital skills and literacy did not necessarily equate to increased engagement with ICT for all participants in this study, rather a range of motivational processes mattered. Implications are considered for technology training and learning for older adults.