This study explored the interplay between contextual and individual factors related to Internet adoption in isolated rural communities. By investigating 10 remote villages throughout Chile that received Internet access infrastructure in 2010–2011, we identified 3 areas in which contextual and individual factors are intertwined. First, the geographical isolation shaped people's personality and attitudes towards new experiences, including digital technologies. Second, the communities' aging population also represented a strong challenge because they lack young people, a relevant technology socialization agent. Finally, jobs and economic activities are related to people's (lack of) motivations and needs towards digital technologies. When the Internet has reached the vast majority of the population, isolated communities confront specific challenges that we need to consider in policy‐making decisions.