Digital literacy is a crucial skill set within the social, political, and economic contexts of 21st-century society. Around the world, governments are making a concerted effort to develop digital literacy within adults, as indicated through Sustainable Development Goal 4. However, working learners from a variety of backgrounds and geographies present unique institutional, situational, and dispositional barriers when seeking digital literacies. Furthermore, digitally disconnected working learners cannot gain the necessary skills to fully participate in 21st-century knowledge economies when trying to cross the first and second digital literacy divides. This article considers how the contexts of different working learners create different needs that adult education practitioners must respond to via whole systems advocacy.