This chapter describes the progress and the challenges of a three-year, small grant-supported project designed to collect, transcribe, code, and analyze interpreted encounters in a variety of institutional settings. In keeping with our project goals, we videotaped nine interpreted interactions, transcribed much of the data, and, with the help of a research assistant, began to code the discourse features in at least three of the transcribed videos. Our discussion focuses on the challenges inherent in a project designed to capture naturalistic data in a wide range of institutional settings. We reflect on our experiences regarding the full research cycle and make recommendations for future interpreting research. In addition, we provide samples from our project, including photos, transcriptions, sample codings, and findings. We also make a case for the benefits of developing a corpus of naturalistic data in the interpreting field, and of developing a body of qualitative analyses of interpreted discourse.