This qualitative study was designed to explore the literacy practices of adolescent boys in digital communities, how their identities are reflected in these practices, and how they move within and across digital spaces. Aspects of identity and community, two key elements of meaning-making through literacy, were studied along with the ways the boys engage within and among digital communities, including video games, social media, group chats, and online forums outside of their time in school. Areas of inquiry were reflections of identity in the literacy practices, literacy practices in affinity and relationship-based digital communities, and movement within and among these digital communities. These areas were explored through the qualitative tools of surveys, semi-structured interviews, co-inquiry group sessions, and collection of artifacts over a 6-week period of time. The study’s findings focused on the ways the boys’ identities were influenced by navigating positions as insiders and outsiders in digital communities and the ways they used literacy practices in these digital spaces to establish and deepen relationships and connections with others.