This chapter conceptualizes the research encounter as an awareness of how research is constructed in time, space, and through participatory interactions—where both research design and practice emerge through dialogue. Concentrating on the hierarchical social contexts of the Caribbean, the authors observe a shift in “learning” from formalized environments toward community-based networks. This highlights a complex learning trajectory informed by varied practices and diverse learning spaces. The Caribbean context thus offers insight into an engaged process of digital learning and skill acquisition, contributing to personal growth and the mastery of digital literacies and fluencies.