In this article we present the methodology and initial results from qualitative research into the usage and communication of digital information. It considers the motivation for the research and the methodologies adopted, including Contextual Design and Cultural Probes. The article describes the preliminary studies conducted to test the approach, highlighting the strengths and limitations of the techniques applied. Finally, it outlines proposals for refinement in subsequent iterations and the future research activities planned. The research is carried out as part of the Planets (Preservation and Long-term Access through NETworked Services) project.