In this paper we present a case study of longitudinal in-situ observation involving a social application for mobile communication. Explorations of new concepts generally suffer from the lack of users’ familiarity, technical issues, and upfront infrastructure cost. This has particular significance for research that relies upon an adequate level of adoption within a community or a social group. Because of the complex interactions between technology, mobile infrastructure, individuals, and social dynamics we require methods that make provisions for uncertainty and ad-hoc inquiry. Our study demonstrates an adaptive approach to planning, design, and implementation that is responsive to social and infrastructure conditions. It represents a shift from traditional longitudinal studies that observe systems with fixed sets of affordances. It counteracts the dynamic social factors and investigations with evolving system features and research methodology. Consequently, it points to the plasticity required from the prototype service to ensure sustained use and adoption.