In 2015, over two hundred million people, around the world, went online for the first time bringing the number of people worldwide using the Internet to 3.2 billion. Still, a majority of the world, about 4.2 billion, is offline. The barriers to going online and becoming digitally literate can be greater than just infrastructural obstacles, including psychosocial barriers related to incentives, affordability, and user capability. Our goal is to help the next 4 billion go online by designing an educational solution to equip people with digital literacy skills to improve their lives. We have employed a human-centered design methodology through community research, synthesis, ideation, and prototyping to build solutions first for northern and central India. The design may be re-contextualized in order to scale to new locations. This paper focuses on the research and synthesis phases of our design process during which we first define digital literacy relevant to the local context and then conducted fieldwork to collect stories, observations and quotes from numerous communities with varying levels of digital literacy. That feedback was translated into insights, themes, and frameworks that will later inform the design and development of an educational technology intervention.