Pilot implementation is a powerful and widely used approach in identifying design flaws and implementation issues before the full-scale deployment of new health information systems. However, pilot implementations often fail in the sense that they say little about the usability and usefulness of the proposed system designs. This calls for studies that seek to uncover and analyze the reasons for failure, so that guidelines for conducting such pilots can be developed. In this paper, we present a qualitative field study of an ambitious, but unsuccessful pilot implementation of a Danish healthcare information system. Based on the findings from this study, we identify three main challenges: (1) defining an appropriate scope for pilot implementation, (2) managing the implementation process, and (3) ensuring commitment to the pilot. Finally, recommendations for future research and implications for practice are provided.