Despite evidence of an upward trend in the adoption of information and communication technologies (ICTs), current media discourse suggests that older adults (those 60-plus) lag behind in terms of engagement with digital technology. Through a survey and interviews with older adults, we investigate how this population views its own digital skills, barriers to digital literacy, and the social and institutional support system it draws on for help with technology. A lack of skills and limited social and institutional systems 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.