As digital technologies continue transforming the time and space boundaries that traditionally had been ascribed to different educational settings, the very notion of learning "context" also is being challenged in educational research literature. In this article, we contribute to this debate by offering an empirically grounded discussion on the contrast between customary notions of context--which emphasize self-containment--and the emerging notion of "learning lives"--which aims to capture the dialectical relation between continuity and transformation that characterizes life processes. We draw from empirical materials collected through a participant ethnography at an arts-based, community-oriented primary school, where we follow the learning lives of school community members as they participate in a theater project, moving between the school and the home settings. Our analyses compare conceptualizations and analytical categories that emphasize "context" and the associated "boundaries" with conceptualizations and units of analysis that emphasize the fluid and boundless character of learning and living across settings and time.