Despite evidence of an upward trend in ICT adoption, current media discourse suggests that older adults (those 60+) lag behind in terms of engagement with digital technology. Through a survey and interviews with older adults we investigate how this population views their own digital skills, barriers to digital literacy, and the social and institutional support system they draw on for technology help. Older adults recognize their age as a factor in the adoption of technology and note differences between how they and younger generations use technology. A lack of skills and limited social and institutional support make it difficult for older adults to gain experience and comfort with technology. However, support systems, such as family and peers, can help mediate older adults’ reluctance with technology. We propose a model with the aim of understanding the needs of older adults in gaining greater digital literacy.